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

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

研究成果: Article査読

9 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)15874-15880
ページ数7
ジャーナルChemistry - A European Journal
22
44
DOI
出版ステータスPublished - 2016 10 24

ASJC Scopus subject areas

  • 触媒
  • 有機化学

フィンガープリント

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