Reaction of Corey ylide with α,β-unsaturated ketones: tuning of chemoselectivity toward dihydrofuran synthesis.

A straightforward, efficient, and reliable approach to synthetically valuable 2,3-dihydrofurans via a reaction between Corey ylide and α,β-unsaturated ketones has been developed. The use of simple and widely spread starting materials as well as mild reaction conditions and scalability provide a broad scope of 2,3-dihydrofurans.

[1]  L. Shimon,et al.  Highly coplanar very long oligo(alkylfuran)s: a conjugated system with specific head-to-head defect. , 2014, Journal of the American Chemical Society.

[2]  Stefan France,et al.  Intramolecular donor-acceptor cyclopropane ring-opening cyclizations. , 2014, Chemical Society reviews.

[3]  S. Chandrasekaran,et al.  Ring opening of activated cyclopropanes with NIS/NaN3: synthesis of C-1 linked pseudodisaccharides , 2013 .

[4]  P. Sridhar,et al.  Ring-contraction vs ring-expansion reactions of spiro-cyclopropanecarboxylated sugars. , 2013, Organic letters.

[5]  D. Stalke,et al.  Rearrangements of Furan‐, Thiophene‐ and N‐Boc‐Pyrrole‐Derived Donor‐Acceptor Cyclopropanes: Scope and Limitations , 2013 .

[6]  P. Zavalij,et al.  Tetrahydroquinolines and benzazepines through catalytic diastereoselective formal [4 + 2]-cycloaddition reactions between donor-acceptor cyclopropenes and imines. , 2013, Organic letters.

[7]  H. Reissig,et al.  Alkylation and Ring Opening of Perfluoroalkyl- and Perfluoroaryl-Substituted 2-Siloxycyclopropanecarboxylates Yielding Fluorinated γ-Oxo Esters or β,γ-Unsaturated Ketones , 2013 .

[8]  H. Reissig,et al.  Trifluoromethanesulfonic acid catalyzed friedel-Crafts alkylations of 1,2,4-trimethoxybenzene with aldehydes or benzylic alcohols. , 2013, Organic letters.

[9]  Peng-mian Huang,et al.  [5C + 1N] annulations: two novel routes to substituted dihydrofuro[3,2-c]pyridines. , 2012, Organic letters.

[10]  Zhongwen Wang.  Polar Intramolecular Cross-Cycloadditions of Cyclopropanes toward Natural Product Synthesis , 2012, Synlett.

[11]  Pei Tang,et al.  Recent Applications of Cyclopropane-Based Strategies to Natural Product Synthesis , 2012 .

[12]  M. Melnikov,et al.  Recent advances in ring-forming reactions of donor–acceptor cyclopropanes , 2011 .

[13]  Haoqiang Lin,et al.  β-(Trifluoromethyl)vinyl sulfonium salts: preparation and reactions with active methylene and methenyl compounds. , 2011, The Journal of organic chemistry.

[14]  Hengbin Wang,et al.  Sequential rhodium-, silver-, and gold-catalyzed synthesis of fused dihydrofurans. , 2011, Organic letters.

[15]  Stefan France,et al.  A catalytic homo-Nazarov cyclization protocol for the synthesis of heteroaromatic ring-fused cyclohexanones. , 2011, Organic letters.

[16]  Xiao‐Qi Yu,et al.  An efficient, transition-metal-free process for the synthesis of substituted dihydrofurans via a Michael/cyclization tandem reaction , 2011 .

[17]  J. Menéndez,et al.  CAN-promoted, diastereoselective synthesis of fused 2,3-dihydrofurans and their transformation into tetrahydroindoles , 2010 .

[18]  M. Bertrand,et al.  A flexible, stereoselective dimethylzinc-mediated radical-anionic cascade: dramatic influence of additional Lewis acids. , 2010, Organic letters.

[19]  Yongcheng Lin,et al.  Design and synthesis of novel xyloketal derivatives and their vasorelaxing activities in rat thoracic aorta and angiogenic activities in zebrafish angiogenesis screen. , 2010, Journal of medicinal chemistry.

[20]  Yong-cheng Lin,et al.  Marine compound Xyloketal B protects PC12 cells against OGD-induced cell damage , 2009, Brain Research.

[21]  M. Kerr,et al.  Heterocycles from cyclopropanes: applications in natural product synthesis. , 2009, Chemical Society reviews.

[22]  Zhong Pei,et al.  A novel marine compound xyloketal B protects against oxidized LDL-induced cell injury in vitro. , 2009, Biochemical pharmacology.

[23]  D. Agrawal,et al.  Silylmethyl-substituted cyclopropyl and other strained ring systems: cycloaddition with dipolarophiles. , 2008, Chemical communications.

[24]  X. Pannecoucke,et al.  New synthesis and cyclopropanation of α-phenylselanyl α,β-unsaturated ketones with non-stabilized phosphorus ylides , 2008 .

[25]  C. Mukai,et al.  Studies of ring-closing mode of 4-hydroxy-2-vinylidenebutanoates: 5-exo-trig versus 5-endo-dig , 2007 .

[26]  X. Liu,et al.  Xyloketal H from the mangrove endophytic fungus Xylaria sp. 2508 , 2006 .

[27]  P. D. Wilson,et al.  Total synthesis of (-)-xyloketal A. , 2006, Organic letters.

[28]  Jeffrey S. Johnson,et al.  Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans. , 2006, Organic letters.

[29]  P. Guiry,et al.  Synthesis of Dihydrofurans Substituted in the 2‐Position , 2005 .

[30]  O. Sterner,et al.  Tridemethylisovelleral, a potent cytotoxic agent. , 2005, Bioorganic & medicinal chemistry.

[31]  Mingjin Fan,et al.  A facile synthesis of highly functionalized dihydrofurans based on 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed reaction of halides with enones , 2005 .

[32]  Francesco Secci,et al.  Regioselective Synthesis of Trisubstituted 2,3-Dihydrofurans from Donor−Acceptor Cyclopropanes or from Reaction of the Corey Ylide with α-Sulfenyl-, α-Sulfinyl-, or α-Sulfonylenones , 2005 .

[33]  Ming‐Shiuan Yu,et al.  Recent advances in donor-acceptor (DA) cyclopropanes , 2005 .

[34]  R. Zimmer,et al.  Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis. , 2003, Chemical reviews.

[35]  P. Brun,et al.  Controlled Synthesis of Functionalized Mixed Thiophene/Furan Oligomers , 2002 .

[36]  I. Kawasaki,et al.  A novel tandem reaction of 3-substituted coumarins with two equivalents of dimethylsulfoxonium ylide to 2-substituted cyclopenta[b]benzofuran-3-ol derivatives , 2002 .

[37]  K. Krohn,et al.  Five unique compounds: xyloketals from mangrove fungus Xylaria sp. from the South China Sea coast. , 2001, The Journal of organic chemistry.

[38]  I. Sattler,et al.  New 1-O-Acyl α-L-Rhamnopyranosides and Rhamnosylated Lactones from Streptomyces sp., Inhibitors of 3α-Hydroxysteroid-dehydrogenase (3α-HSD) , 2000 .

[39]  E. Wenkert,et al.  Reactions of ethyl diazoacetate with β-methylfurans , 1999 .

[40]  S. Thompson,et al.  Total synthesis of some marasmane and lactarane sesquiterpenes , 1992 .

[41]  E. Corey,et al.  Dimethyloxosulfonium Methylide ((CH3)2SOCH2) and Dimethylsulfonium Methylide ((CH3)2SCH2). Formation and Application to Organic Synthesis , 1965 .

[42]  H. Reissig,et al.  Synthesis of Functionalized, Sterically Congested Calix[4]phyrin Macrocycles Using Donor–Acceptor‐Substituted Cyclopropanes – First Example of a Mono‐meso‐spirolactone Incorporated into a Calix[4]phyrin , 2013 .

[43]  V. P. Lysenko,et al.  Twenty-five years of dimethylsulfoxonium methylide (Corey's reagent) , 1987 .

[44]  Carl R. Johnson,et al.  S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles , 1980 .