Asymmetric Formal [3+2] Cycloaddition Reaction of Succinaldehyde and Nitroalkene Catalyzed by Diphenylprolinol Silyl Ether

研究成果: Article査読

9 被引用数 (Scopus)

抄録

The enantioselective domino Michael/Henry reaction of nitroalkenes with succinaldehyde was found to proceed efficiently upon using diphenylprolinol silyl ether as the organocatalyst. The reaction affords cis-disubstituted nitropentenes with excellent diastereoselectivities and enantioselectivities after treatment of the Michael product with Ac2O and pyridine. cis-Disubstituted nitropentenes are obtained with excellent diastereoselectivities and enantioselectivities by a formal [3+2] cycloaddition reaction. The first reaction is a domino reaction composed of the diphenylprolinol silyl ether mediated Michael reaction of nitroalkene with succinaldehyde followed by a Henry reaction. The next reaction is a dehydration achieved by using Ac2O and pyridine.

本文言語English
ページ(範囲)4320-4324
ページ数5
ジャーナルEuropean Journal of Organic Chemistry
2015
20
DOI
出版ステータスPublished - 2015 7月 1

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 有機化学

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