Journal ArticleDOI
Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction.
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TLDR
In this article, the authors describe a catalytic enantioselective Mukaiyama aldol reaction, which is catalyzed by a newly designed chiral disulfonimide and delivers chiral allenoates in high yields and with excellent regio-, diastereo-, and enanti-lectivity.Abstract:
Herein we describe the development of a catalytic enantioselective alkynylogous Mukaiyama aldol reaction. The reaction is catalyzed by a newly designed chiral disulfonimide and delivers chiral allenoates in high yields and with excellent regio-, diastereo-, and enantioselectivity. Our process tolerates a broad range of aldehydes in combination with diverse alkynyl-substituted ketene acetals. The reaction products can be readily derivatized to furnish a variety of highly substituted enantiomerically enriched building blocks.read more
Citations
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Journal ArticleDOI
Organocatalytic Enantioselective Synthesis of Chiral Allenes: Remote Asymmetric 1,8‐Addition of Indole Imine Methides
Xing Guang Li,Jianwei Sun +1 more
TL;DR: An organocatalytic enantioconvergent synthesis of chiral tetrasubstituted allenes is disclosed and a mechanism involving remotely controlled asymmetric 1,8-addition of the in situ-generated indole imine methide via a bifunctional transition state is suggested.
Journal ArticleDOI
Copper‐Catalyzed Asymmetric Coupling of Allenyl Radicals with Terminal Alkynes to Access Tetrasubstituted Allenes
Xiao-Yang Dong,Tian-Ya Zhan,Sheng-Peng Jiang,Xiao-Dong Liu,Liu Ye,Zhong-Liang Li,Qiang-Shuai Gu,Xin-Yuan Liu +7 more
TL;DR: A copper-catalyzed asymmetric radical 1,4-carboalkynylation of 1,3-enynes via the coupling of allenyl radicals with terminal alkynes is described, providing diverse synthetically challenging tetrasubstituted chiral allenes.
Journal ArticleDOI
Organocatalytic Enantioselective Synthesis of Tetrasubstituted α-Amino Allenoates by Dearomative γ-Addition of 2,3-Disubstituted Indoles to β,γ-Alkynyl-α-imino Esters.
TL;DR: This methodology allows access to a series of highly functionalized tetrasubstituted allenes featuring adjacent quaternary stereocenter in high yields, with excellent regio-, diastereo-, and enantioselectivities under mild conditions without generation of any waste.
Journal ArticleDOI
Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives.
Pernille H. Poulsen,Yang Li,Vibeke Henriette Lauridsen,Danny K. B. Jørgensen,Teresa A. Palazzo,Marta Meazza,Karl Anker Jørgensen +6 more
TL;DR: A novel reaction that provides chiral allenes by amino catalytic activation of either aldehydes or α,β-unsaturated aldehyde for reaction with alkynyl-substituted enones is presented and the utility of the reaction concept is demonstrated by the synthesis of chiral furan derivatives in high yields and stereoselectivities.
Journal ArticleDOI
Coarctate and Möbius: The Helical Orbitals of Allene and Other Cumulenes.
TL;DR: The origins and detailed composition of the helical orbitals of cumulenes are traced, which emerge in the simplest Hückel model and are not much modified in advanced computations.
References
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Journal ArticleDOI
Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction
TL;DR: The reaction is catalyzed by a newly designed chiral disulfonimide and delivers chiral allenoates in high yields and with excellent regio-, diastereo-, and enantioselectivity.