Asymmetric Diels–Alder Reaction of α‐Substituted and β,β‐Disubstituted α,β‐Enals via Diarylprolinol Silyl Ether for the Construction of All‐Carbon Quaternary Stereocenters

By Yujiro Hayashi, Bojan P. Bondzic, Tatsuya Yamazaki, Yogesh Gupta, Shin Ogasawara, Tohru Taniguchi,  Kenji Monde

November 2, 2018

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Title

Asymmetric Diels–Alder Reaction of α‐Substituted and β,β‐Disubstituted α,β‐Enals via Diarylprolinol Silyl Ether for the Construction of All‐Carbon Quaternary Stereocenters

Author

Yujiro Hayashi, Bojan P. Bondzic, Tatsuya Yamazaki, Yogesh Gupta, Shin Ogasawara, Tohru Taniguchi,  Kenji Monde

Year

2016

Journal

Chemistry a European Journal

Abstract

The asymmetric Diels–Alder reaction of α‐substituted acrolein proceeds in the presence of the trifluoroacetic acid salt of trifluoromethyl‐substituted diarylprolinol silyl ether to afford the exo‐isomer with both excellent diastereoselectivity and high enantioselectivity. In the Diels–Alder reaction of a β,β‐disubstituted α,β‐unsaturated aldehyde, good exo‐selectivity and excellent enantioselectivity was obtained when the perchloric acid salt of the bulky triisopropyl silyl ether of trifluoromethyl substituted diarylprolinol was employed as an organocatalyst in the presence of water. In both cases, all‐carbon quaternary stereocenters are constructed enantioselectively.

Full Article

https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201602345

Instrument

FVS-6000

Keywords

Vibrational circular dichroism,