Ligand-controlled enantioselective [2 + 2] cycloaddition of oxabicyclic alkenes with terminal alkynes using chiral iridium catalysts.

The first catalytic asymmetric [2 + 2] cycloaddition of oxabicyclic alkenes and terminal alkynes has been developed. This iridium-catalyzed enantioselective [2 + 2] cycloaddition allows the formation of four stereocenters in a single step with excellent enantioselectivity (94-->99% ee).

[1]  Z. Shao,et al.  Combining transition metal catalysis and organocatalysis: a broad new concept for catalysis. , 2009, Chemical Society reviews.

[2]  W. Tam,et al.  Transition Metal-Catalyzed [2+2] Cycloaddition Reactions between Bicyclic Alkenes and Alkynes , 2009 .

[3]  A. Chan,et al.  Enantioselective, copper(I)-catalyzed three-component reaction for the synthesis of β,γ-alkynyl α-amino acid derivatives , 2009 .

[4]  A. Chan,et al.  Unprecedented Effects of Additives and Ligand‐to‐Metal Ratio on the Enantiofacial Selection of Copper‐Catalyzed Alkynylation of α‐Imino Ester with Arylacetylenes , 2007 .

[5]  W. Tam,et al.  Study on the reactivity of oxabicyclic alkenes in ruthenium-catalyzed [2+2] cycloadditions. , 2007, The Journal of organic chemistry.

[6]  Chien‐Hong Cheng,et al.  New catalytic reactions of oxa- and azabicyclic alkenes. , 2007, Accounts of chemical research.

[7]  Tamio Hayashi,et al.  Rhodium-catalyzed asymmetric cyclodimerization of oxa- and azabicyclic alkenes. , 2007, Journal of the American Chemical Society.

[8]  W. Tam,et al.  Ruthenium‐Catalyzed [2 + 2] Cycloadditions Between C1‐Substituted 7‐Oxanorbornadienes and Alkynes. , 2006 .

[9]  R. Takeuchi,et al.  Iridium-Catalyzed Formation of Carbon-Carbon and Carbon-Heteroatom Bonds , 2006 .

[10]  L. Giordano,et al.  Herrmann-Beller phosphapalladacycle-catalyzed addition of alkynes to norbornadienes. , 2006, Organic letters.

[11]  T. Shibata,et al.  Rh-catalyzed enantioselective [2 + 2] cycloaddition of alkynyl esters and norbornene derivatives. , 2006, Organic letters.

[12]  Karine Villeneuve,et al.  Asymmetric induction in ruthenium-catalyzed [2+2] cycloadditions between bicyclic alkenes and a chiral acetylenic acyl sultam. , 2004, Angewandte Chemie.

[13]  M. Lautens,et al.  Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes. , 2003, Accounts of chemical research.

[14]  Chien‐Hong Cheng,et al.  Highly stereoselective ring-opening addition of terminal acetylenes to bicyclic olefins catalyzed by nickel complexes. , 2002, Organic letters.

[15]  Chien‐Hong Cheng,et al.  Cross [2 + 2] cycloaddition of bicyclic alkenes with alkynes mediated by cobalt complexes: a facile synthesis of cyclobutene derivatives. , 2001, The Journal of organic chemistry.

[16]  Chien‐Hong Cheng,et al.  Nickel‐Catalyzed [2+2] Cycloaddition of Alkynes with Activated Cyclic Alkenes: Synthesis and Novel Ring Expansion Studies of Cyclobutene Products , 2000 .

[17]  Claibourne D. Smith Cycloaddition Reactions of “Quadricyclanes”1 , 1966 .

[18]  Y. Meinwald,et al.  The Addition of Nitrosyl Halides to Olefins. Dependence of Steric Course on Olefin Structure , 1964 .

[19]  Chien‐Hong Cheng,et al.  Stereoselective [2 + 2 + 2] cocyclotrimerization of oxa- and azabenzonorbornadienes with alkynes catalyzed by nickel complexes: first transition metal-mediated synthesis of isobenzofuran and isoindole precursors , 2000 .

[20]  Chien‐Hong Cheng,et al.  Nickel-catalyzed cocyclotrimerization of oxa- and azabenzonorbornadienes with alkynes: reaction with multiple synthetic applications , 1998 .