☆ 4.8 Article

Asymmetric Catalytic Conjugate Addition of Acetaldehyde to Nitrodienynes/Nitroenynes: Applications to the Syntheses of (+)-α-Lycorane and Chiral β-Alkynyl Acids

ORGANIC LETTERS (2014)

期刊

ORGANIC LETTERS

卷 16, 期 11, 页码 3044-3047

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol501158b

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类别

Chemistry, Organic

资金

NSFC [21162034, 21372193, 21362040]
Program for Changjiang Scholars and Innovative Research Team in University [IRT13095]
Doctoral Fund of Ministry of Education of China [20135301110002]
Government of Yunnan Province [2012FB114, 2013FA026]
Program for Excellent Young Talents, Yunnan University

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Reagent

摘要

The catalytic enantioselective conjugate addition of acetaldehyde to polyconjugated substrates, nitrodienynes and nitroenynes, has been accomplished using organocatalysis. Various functionalized 1,3-enynes and propargylic compounds were obtained in moderate to good yields with high enantioselectivity. The synthetic utilities of the conjugate addition reactions have been highlighted in the concise total synthesis of (+)-alpha-lycorane and the metal-free synthesis of chiral beta-alkynyl acids.

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