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催化不对称施陶丁格反应应用于乙烯基氧化膦和乙烯基膦酸酯。

Catalytic asymmetric stetter reaction onto vinylphosphine oxides and vinylphosphonates.

作者信息

Cullen Steven C, Rovis Tomislav

机构信息

Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.

出版信息

Org Lett. 2008 Jul 17;10(14):3141-4. doi: 10.1021/ol801047k. Epub 2008 Jun 13.

DOI:10.1021/ol801047k
PMID:18549233
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2746454/
Abstract

An intramolecular Stetter reaction of vinylphosphine oxides and vinylphosphonates has been developed. Treatment of an aldehyde with a nucleophilic N-heterocyclic carbene catalyst allows for addition of an acyl anion equivalent into a vinylphosphine oxide or vinylphosphonate Michael acceptor in yields up to 99% and ee values up to 96%.

摘要

已开发出乙烯基氧化膦和乙烯基膦酸酯的分子内施陶丁格反应。用亲核性氮杂环卡宾催化剂处理醛，可将酰基阴离子等价物加成到乙烯基氧化膦或乙烯基膦酸酯迈克尔受体中，产率高达99%，对映体过量值高达96%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/31ebbbbc9b5c/nihms140551f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/4804ed7d5095/nihms140551f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/8b92bd659143/nihms140551f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/32ff5d187f98/nihms140551f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/31ebbbbc9b5c/nihms140551f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/4804ed7d5095/nihms140551f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/8b92bd659143/nihms140551f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/32ff5d187f98/nihms140551f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ccc/2746454/31ebbbbc9b5c/nihms140551f4.jpg

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