Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction

Tap, Aurélien; Blond, Aurélie; Wakchaure, V. N.; List, Benjamin

doi:10.1002/anie.201603649

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Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction

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Tap, Aurélien
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Blond, Aurélie
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wakchaure, V. N.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Tap, A., Blond, A., Wakchaure, V. N., & List, B. (2016). Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction. Angewandte Chemie International Edition, 55(31), 8962-8965. doi:10.1002/anie.201603649.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-0B01-1

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.