Catalytic enantioselective allylboration of propargylic aldehydes

[1]  Chun‐hui Xing,et al.  Asymmetric Allylboration of Aldehydes with Pinacol Allylboronates Catalyzed by 1,1′‐Spirobiindane‐7,7′‐diol (SPINOL) Based Phosphoric Acids , 2012 .

[2]  Stephen Ho,et al.  A more comprehensive and highly practical solution to enantioselective aldehyde crotylation. , 2011, Journal of the American Chemical Society.

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

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

[5]  D. Hall,et al.  Rationally improved chiral Brønsted acid for catalytic enantioselective allylboration of aldehydes with an expanded reagent scope. , 2009, The Journal of organic chemistry.

[6]  M. Krische,et al.  anti-Diastereo- and enantioselective carbonyl crotylation from the alcohol or aldehyde oxidation level employing a cyclometallated iridium catalyst: alpha-methyl allyl acetate as a surrogate to preformed crotylmetal reagents. , 2009, Journal of the American Chemical Society.

[7]  A. Fürstner,et al.  A gold-catalyzed entry into the sesquisabinene and sesquithujene families of terpenoids and formal total syntheses of cedrene and cedrol. , 2008, Chemistry.

[8]  Michael J. Krische,et al.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl addition. , 2008, Journal of the American Chemical Society.

[9]  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.

[10]  D. Curran,et al.  Confirmation of the stereostructure of (+)-cytostatin by fluorous mixture synthesis of four candidate stereoisomers. , 2008, Angewandte Chemie.

[11]  D. Hall.  New preparative methods for allylic boronates and their application in stereoselective catalytic allylborations , 2008 .

[12]  J. Wzorek,et al.  Control of skeletal connectivity in indium promoted reactions: 1,2-additions and cope rearrangements en route to lactol formation. , 2007, The Journal of organic chemistry.

[13]  D. Hall,et al.  Catalytic enantioselective and catalyst-controlled diastereofacial-selective additions of allyl- and crotylboronates to aldehydes using chiral Brønsted acids. , 2006, Angewandte Chemie.

[14]  F. Carreaux,et al.  Catalytic enantioselective three-component hetero-[4+2] cycloaddition/allylboration approach to alpha-hydroxyalkyl pyrans: scope, limitations, and mechanistic proposal. , 2006, Chemistry.

[15]  J. Férézou,et al.  The Application of [γ‐(Silyloxy)allylidene]ditin to the Efficient Synthesis of the Chromophore of the Neocarzinostatin Dihydroxycyclopentene‐Based Dienediyne Core , 2006 .

[16]  D. Hall,et al.  Additions of functionalized α-substituted allylboronates to aldehydes under the novel Lewis and Brønsted acid catalyzed manifolds , 2005 .

[17]  J. Soderquist,et al.  Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes. , 2005, Journal of the American Chemical Society.

[18]  M. Kurosu,et al.  Effect of water on Keck's catalytic asymmetric allylations of aldehydes , 2005 .

[19]  J. L. Leighton,et al.  Highly diastereo- and enantioselective reagents for aldehyde crotylation. , 2004, Organic letters.

[20]  W. Roush,et al.  Synthesis of the C11-C29 fragment of amphidinolide F. , 2004, Organic letters.

[21]  A. Fürstner,et al.  Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes. , 2004, Journal of the American Chemical Society.

[22]  W. Roush,et al.  Total synthesis of cochleamycin A. , 2004, Organic letters.

[23]  Â. Fátima,et al.  Total syntheses of (R)-argentilactone and (R)-goniothalamin via catalytic enantioselective allylation of aldehydes , 2003 .

[24]  K. Nicolaou,et al.  Total synthesis of apoptolidin: construction of enantiomerically pure fragments. , 2003, Journal of the American Chemical Society.

[25]  D. Hall,et al.  Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols. , 2003, Journal of the American Chemical Society.

[26]  S. Denmark,et al.  Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones. , 2003, Chemical reviews.

[27]  S. A. Burova,et al.  Stereoselective synthesis of a family of alternating polyols from six-carbon epoxyalkynol modules. , 2002, Journal of the American Chemical Society.

[28]  Pui Yee Ng,et al.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes. , 2002, Journal of the American Chemical Society.

[29]  J. Falck,et al.  Asymmetric total synthesis of (+)-fostriecin. , 2002, Organic letters.

[30]  M. Kurosu,et al.  Catalytic asymmetric allylations of achiral and chiral aldehydes via BINOL–Zr complex , 2002 .

[31]  E. Carreira,et al.  Facile enantioselective synthesis of a key homoallylic alcohol building block for polyketide synthesis: TiF4–BINOL catalyzed allylsilylation with allyl trimethylsilane , 2001 .

[32]  S. Denmark,et al.  Lewis base activation of Lewis acids: catalytic enantioselective allylation and propargylation of aldehydes. , 2001, Journal of the American Chemical Society.

[33]  Junha Jeon,et al.  Catalytic Asymmetric Allylic Transfer Reactions for the Enantioselective Synthesis of Dienyl and Enynyl Alcohols , 2001 .

[34]  J. Cossy,et al.  Enantioselective synthesis of propargylic alcohols by addition of enantiopure cyclopentadienyldialkoxyallyltitanium complexes to acetylenic aldehydes , 2000 .

[35]  E. Corey,et al.  Enantioselective Total Synthesis of Nicandrenones , 2000 .

[36]  Hisashi Yamamoto,et al.  Enantioselective Protonation of Silyl Enol Ethers and Ketene Disilyl Acetals with Lewis Acid-Assisted Chiral Brønsted Acids: Reaction Scope and Mechanistic Insights , 2000 .

[37]  J. Otera,et al.  Modern Carbonyl Chemistry , 2000 .

[38]  P. Ramachandran,et al.  An Efficient Enantioselective Synthesis of Argentilactone. , 1999 .

[39]  H. Fujimoto,et al.  THEORETICAL STUDY OF THE EFFECTS OF STRUCTURE AND SUBSTITUENTS ON REACTIVITY IN ALLYLBORATION , 1998 .

[40]  J. A. Marshall,et al.  Enantioselective and Diastereoselective Additions of Allylic Stannanes to Aldehydes Promoted by a Chiral (Acyloxy)borane Catalyst , 1998 .

[41]  Amos B. Smith,et al.  Total Syntheses of (−)-Macrolactin A, (+)-Macrolactin E, and (−)-Macrolactinic Acid: An Exercise in Stille Cross-Coupling Chemistry , 1998 .

[42]  Amos B. Smith,et al.  Total synthesis of -macrolactin A , 1996 .

[43]  K. Ishihara,et al.  First Example of a Highly Enantioselective Catalytic Protonation of Silyl Enol Ethers Using a Novel Lewis Acid-Assisted Brønsted Acid System , 1996 .

[44]  Hisashi Yamamoto,et al.  Lewis Acid Assisted Chiral Bronsted Acid for Enantioselective Protonation of Silyl Enol Ethers and Ketene Bis(trialkylsilyl) Acetals , 1994 .

[45]  G. E. Keck,et al.  Catalytic asymmetric allylation (CAA) reactions. II. A new enantioselective allylation procedure , 1993 .

[46]  M. Grier,et al.  Catalytic asymmetric allylation reactions. 3. Extension to methallylstannane, comparison of procedures, and observation of a nonlinear effect , 1993 .

[47]  G. E. Keck,et al.  Catalytic asymmetric allylation of aldehydes , 1993 .

[48]  Yoshinori Yamamoto,et al.  SELECTIVE REACTIONS USING ALLYLIC METALS , 1993 .

[49]  G. Linstrumelle,et al.  An efficient stereocontrolled synthesis of 12(R)-HETE and 12(S)-HETE , 1992 .

[50]  Michael G. Yang,et al.  Diastereofacial selectivity with optically active .alpha.-substituted .beta.-silyl-(E)-hexenoates. Enantioselective construction of homoallylic ethers via reaction with aryl acetals , 1991 .

[51]  K. Furuta,et al.  Chiral (Acyloxy)borane Catalyzed Asymmetric Allylation of Aldehydes , 1992 .

[52]  P. Pellechia,et al.  Organoboranes. 53. A high-field variable-temperature proton and boron-11 NMR study of the effects of solvent and structure on reactivity in allylboration , 1990 .

[53]  H. X. Zhang,et al.  Palladium- and molybdenum-catalyzed hydrostannation of alkynes: a novel access to regio- and stereodefined vinylstannanes , 1990 .

[54]  W. Roush,et al.  Use of metal carbonyl complexes to achieve high enantioselectivity in the asymmetric allylboration of unsaturated aldehydes , 1990 .

[55]  E. Corey,et al.  A practical and efficient method for enantioselective allylation of aldehydes , 1989 .

[56]  R. Duthaler,et al.  Enantioselective Allylation of Carbonyl Compounds with Titanium‐Carbohydrate Complexes , 1989 .

[57]  S. Masamune,et al.  Asymmetric allylboration with B-allyl-2-(trimethylsilyl)borolane , 1989 .

[58]  K. Houk,et al.  Transition structures for the allylboration reactions of formaldehyde by allylborane and allylboronic acid , 1989 .

[59]  J. A. Marshall,et al.  Synthesis of nonracemic y-alkoxy allylstannanes by stereospecific anti[1,3]-stannyl migration , 1989 .

[60]  M. Reetz.  Asymmetric C-C bond formation using organometallic chemistry , 1988 .

[61]  B. Dehoff,et al.  The synthesis of cembranolide precursors via addition of allylstannanes to conjugated aldehydes , 1986 .

[62]  W. Roush,et al.  Diastereo- and enantioselective aldehyde addition reactions of 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylic esters, a useful class of tartrate ester modified allylboronates , 1985 .

[63]  T. Nakai,et al.  APPLICATION OF ASYMMETRIC [2,3]WITTIG REARRANGEMENT TO STEREOCONTROL OVER THREE CONTIGUOUS CHIRAL CENTERS. A NEW SYNTHESIS OF (+)-BLASTMYCINONE , 1985 .

[64]  G. A. Russel,et al.  Stereospecific vinyl substitutions occurring by free radical addition-elimination , 1985 .

[65]  P. Jadhav,et al.  Asymmetric carbon-carbon bond formation via .beta.-allyldiisopinocampheylborane. Simple synthesis of secondary homoallylic alcohols with excellent enantiomeric purities , 1983 .

[66]  S. Denmark,et al.  (E)-3-(Trimethylsilyl)-2-propen-1-ol. An Improved Preparation , 1983 .

[67]  M. Kumada,et al.  Optically active allylsilanes. 2. High stereoselectivity in asymmetric reaction with aldehydes producing homoallylic alcohols , 1982 .

[68]  R. Hoffmann,et al.  Stereoselektive Synthese von Alkoholen, VII1) Optisch aktive Homoallylalkohole durch Addition chiraler Boronsäureester an Aldehyde , 1981 .

[69]  H. Brown,et al.  Hydroboration. 54. New general synthesis of alkyldihaloboranes via hydroboration of alkenes with dihaloborane-dimethyl sulfide complexes. Unusual trends in the reactivities and directive effects , 1980 .

[70]  R. W. Hoffmann,et al.  Enantioselective Synthesis of Homoallyl Alcohols via Chiral Allylboronic Esters , 1978 .

[71]  C. Brown,et al.  Catalytic hydrogenation. VI. Reaction of sodium borohydride with nickel salts in ethanol solution. P-2 Nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure , 1973 .

[72]  R. Steele,et al.  Novel method for the synthesis of cis-.alpha.,.beta.-unsaturated derivatives trans-hydroalumination of disubstituted alkynes with lithium diisobutylmethylaluminum hydride , 1967 .

[73]  R. Steele,et al.  A new and convenient method for the preparation of isomerically pure .alpha.,.beta.-unsaturated derivatives via hydroalumination of alkynes , 1967 .