Recent Advances in the Preparation and Application of Allylboron Species in Organic Synthesis.

In this Perspective we will highlight the most important recent breakthroughs in selective allylboron chemistry (both the synthesis and application of these species). In addition we will provide an outlook toward the future of this promising subfield of organic synthesis.

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[29]  Hajime Ito,et al.  Copper(I)-catalyzed enantioselective synthesis of α-chiral linear or carbocyclic (E)-(γ-alkoxyallyl)boronates. , 2014, Journal of the American Chemical Society.

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[36]  F. Himo,et al.  Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines , 2014 .

[37]  K. Szabó,et al.  Borylation of propargylic substrates by bimetallic catalysis. Synthesis of allenyl, propargylic, and butadienyl Bpin derivatives. , 2014, Journal of the American Chemical Society.

[38]  Marvin Lübcke,et al.  A diastereoselective one-pot, three-step cascade toward α-substituted allylboronic esters. , 2014, The Journal of organic chemistry.

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[40]  R. Batey,et al.  An organotrifluoroborate-based convergent total synthesis of the potent cancer cell growth inhibitory depsipeptides kitastatin and respirantin. , 2014, Organic letters.

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[42]  Jeremy R. Duvall,et al.  Catalytic asymmetric allylation of carbonyl compounds and imines with allylic boronates , 2014 .

[43]  Chunrui Sun,et al.  A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates , 2014, Journal of the American Chemical Society.

[44]  I. Marek,et al.  All-carbon quaternary stereogenic centers in acyclic systems through the creation of several C-C bonds per chemical step. , 2014, Journal of the American Chemical Society.

[45]  C. Crudden,et al.  Enantiospecific, regioselective cross-coupling reactions of secondary allylic boronic esters. , 2013, Chemistry.

[46]  Peng‐Fei Xu,et al.  Heterogeneous and homogeneous chiral Cu(II) catalysis in water: enantioselective boron conjugate additions to dienones and dienoesters. , 2013, Chemical communications.

[47]  D. Hall,et al.  Concise synthesis and antimalarial activity of all four mefloquine stereoisomers using a highly enantioselective catalytic borylative alkene isomerization. , 2013, Angewandte Chemie.

[48]  S. Buchwald,et al.  Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides. , 2013, Journal of the American Chemical Society.

[49]  J. Bäckvall,et al.  Control of Selectivity in Palladium-Catalyzed Oxidative Carbocyclization/Borylation of Allenynes , 2013, Angewandte Chemie.

[50]  Mihai Raducan,et al.  Selective formation of adjacent stereocenters by allylboration of ketones under mild neutral conditions. , 2013, Organic letters.

[51]  S. Fustero,et al.  Relay Catalysis: Enantioselective Synthesis of Cyclic Benzo‐Fused Homoallylic Alcohols by Chiral Brønsted Acid‐Catalyzed Allylboration/Ring Closing Metathesis , 2013 .

[52]  M. Yus,et al.  Diastereoselective allylation of carbonyl compounds and imines: application to the synthesis of natural products. , 2013, Chemical reviews.

[53]  C. Willis,et al.  Highly diastereo- and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters. , 2013, Journal of the American Chemical Society.

[54]  J. Morken,et al.  Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate. , 2013, Organic letters.

[55]  I. A. Roundtree,et al.  A catalytic enantioselective tandem allylation strategy for rapid terpene construction: application to the synthesis of pumilaside aglycon. , 2013, Journal of the American Chemical Society.

[56]  K. Houk,et al.  Origins of stereoselectivities in chiral phosphoric acid catalyzed allylborations and propargylations of aldehydes. , 2013, The Journal of organic chemistry.

[57]  R. Batey,et al.  Regio- and stereoselective allylation and crotylation of indoles at C2 through the use of potassium organotrifluoroborate salts. , 2013, Angewandte Chemie.

[58]  K. Szabó,et al.  Mechanistic investigation of the palladium-catalyzed synthesis of allylic silanes and boronates from allylic alcohols. , 2013, Journal of the American Chemical Society.

[59]  M. Snapper,et al.  Simple Organic Molecules as Catalysts for Enantioselective Synthesis of Amines and Alcohols , 2012, Nature.

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[61]  Jennifer L. Farmer,et al.  Regioselective cross-coupling of allylboronic acid pinacol ester derivatives with aryl halides via Pd-PEPPSI-IPent. , 2012, Journal of the American Chemical Society.

[62]  N. Vanthuyne,et al.  Copper Carbenoid, Reactant and Catalyst for One-Pot Diazo Ester Coupling Cascade Rearrangement of Enediynes: Formation of Two Contiguous Tetrasubstituted Stereocenters , 2012 .

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[66]  J. Morken,et al.  Catalytic enantioselective 1,2-diboration of 1,3-dienes: versatile reagents for stereoselective allylation. , 2012, Angewandte Chemie.

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[68]  M. Ueno,et al.  Chiral zinc-catalyzed asymmetric α-alkylallylation and α-chloroallylation of aldehydes. , 2011, Angewandte Chemie.

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[72]  J. Morken,et al.  Catalytic enantioselective diboration of cyclic dienes. A modified ligand with general utility. , 2011, The Journal of organic chemistry.

[73]  J. Morken,et al.  Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling. , 2011, Journal of the American Chemical Society.

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[75]  M. Snapper,et al.  Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C1-symmetric NHC-Cu complexes. , 2011, Journal of the American Chemical Society.

[76]  Hershel H. Lackey,et al.  Stereoconvergent synthesis of chiral allylboronates from an E/Z mixture of allylic aryl ethers using a 6-NHC-Cu(I) catalyst. , 2011, Journal of the American Chemical Society.

[77]  K. Szabó,et al.  Palladium-catalyzed allylic C-OH functionalization for efficient synthesis of functionalized allylsilanes. , 2011, Journal of the American Chemical Society.

[78]  J. Antilla,et al.  Chiral Brønsted acid-catalyzed allylboration of aldehydes. , 2010, Journal of the American Chemical Society.

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[80]  J. Morken,et al.  Pd-catalyzed enantioselective allyl-allyl cross-coupling. , 2010, Journal of the American Chemical Society.

[81]  A. Hoveyda,et al.  Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions. , 2010, Journal of the American Chemical Society.

[82]  W. Roush,et al.  Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol. , 2010, Organic letters.

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[84]  Stephen P. Thomas,et al.  Application of the lithiation-borylation reaction to the preparation of enantioenriched allylic boron reagents and subsequent in situ conversion into 1,2,4-trisubstituted homoallylic alcohols with complete control over all elements of stereochemistry. , 2010, Journal of the American Chemical Society.

[85]  U. Schneider,et al.  Indium(I)-catalyzed asymmetric allylation, crotylation, and alpha-chloroallylation of hydrazones with rare constitutional and high configurational selectivities. , 2010, Angewandte Chemie.

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[87]  K. Matsuura,et al.  Desymmetrization of meso-2-alkene-1,4-diol derivatives through copper(I)-catalyzed asymmetric boryl substitution and stereoselective allylation of aldehydes. , 2010, Angewandte Chemie.

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[90]  David S. Barnett,et al.  The mechanism and an improved asymmetric allylboration of ketones catalyzed by chiral biphenols. , 2009, Angewandte Chemie.

[91]  K. Szabó,et al.  Functionalization of unactivated alkenes through iridium-catalyzed borylation of carbon-hydrogen bonds. Mechanism and synthetic applications. , 2009, The Journal of organic chemistry.

[92]  D. Hall,et al.  Catalytic asymmetric synthesis of palmerolide A via organoboron methodology. , 2009, Journal of the American Chemical Society.

[93]  T. Ritter,et al.  Iron-catalyzed 1,4-hydroboration of 1,3-dienes. , 2009, Journal of the American Chemical Society.

[94]  C. Valdés,et al.  Metal-free carbon–carbon bond-forming reductive coupling between boronic acids and tosylhydrazones , 2009, Nature Chemistry.

[95]  J. Morken,et al.  Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration. , 2009, Journal of the American Chemical Society.

[96]  D. Hall,et al.  Alpha-hydroxyalkyl heterocycles via chiral allylic boronates: Pd-catalyzed borylation leading to a formal enantioselective isomerization of allylic ether and amine. , 2009, Journal of the American Chemical Society.

[97]  K. Szabó,et al.  Performance of SCS palladium pincer complexes in borylation of allylic alcohols. Control of the regioselectivity in the one-pot borylation-allylation process. , 2009, The Journal of organic chemistry.

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[100]  Yasunori Yamamoto,et al.  γ-Selective Cross-Coupling Reactions of Potassium Allyltrifluoroborates with Haloarenes Catalyzed by a Pd(0)/D-t-BPF or Pd(0)/Josiphos ((R,S)-CyPF-t-Bu) Complex: Mechanistic Studies on Transmetalation and Enantioselection , 2009 .

[101]  Jonathan M Goodman,et al.  Mechanistic insights into the catalytic asymmetric allylboration of ketones: Brønsted or Lewis acid activation? , 2009, Organic letters.

[102]  K. Szabó,et al.  Synthesis of Stereodefined Substituted Cycloalkenes by a One‐Pot Catalytic Boronation–Allylation–Metathesis Sequence , 2008 .

[103]  V. Aggarwal,et al.  Direct synthesis of functionalized allylic boronic esters from allylic alcohols and inexpensive reagents and catalysts , 2008 .

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[105]  D. Hall,et al.  Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations. , 2008, Journal of the American Chemical Society.

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[110]  K. Matsuura,et al.  Copper-catalyzed enantioselective substitution of allylic carbonates with diboron: an efficient route to optically active alpha-chiral allylboronates. , 2007, Journal of the American Chemical Society.

[111]  K. Szabó,et al.  Petasis Borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. an efficient one-pot route to stereodefined alpha-amino acids and homoallyl alcohols. , 2007, Journal of the American Chemical Society.

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[113]  U. Schneider,et al.  Catalytic activation of pinacolyl allylboronate with indium(I): development of a general catalytic allylboration of ketones. , 2007, Angewandte Chemie.

[114]  D. Hall,et al.  Catalytic enantioselective preparation of alpha-substituted allylboronates: one-pot addition to functionalized aldehydes and a route to chiral allylic trifluoroborate reagents. , 2007, Angewandte Chemie.

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[117]  D. Hall,et al.  Preparation of α-substituted allylboronates by chemoselective iridium-catalyzed asymmetric allylic alkylation of 1-propenylboronates , 2007 .

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[120]  S. Schaus,et al.  Asymmetric allylboration of ketones catalyzed by chiral diols. , 2006, Journal of the American Chemical Society.

[121]  K. Szabó,et al.  Highly Selective and Robust Palladium-Catalyzed Carbon–Carbon Coupling between Allyl Alcohols and Aldehydes via Transient Allylboronic Acids , 2006 .

[122]  T. Wu,et al.  Asymmetric allylboration of cyclic imines and applications to alkaloid synthesis. , 2006, Journal of the American Chemical Society.

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