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有机催化对映选择性合成苯并氧杂硼杂环戊烷：α-甲酰基硼酸的维蒂希/氧杂迈克尔反应串联

Organocatalytic, enantioselective synthesis of benzoxaboroles Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids.

作者信息

Hazra Gurupada, Maity Sanjay, Bhowmick Sudipto, Ghorai Prasanta

机构信息

Department of Chemistry , Indian Institute of Science Education and Research Bhopal , Bhopal By-pass Road, Bhauri , Bhopal-462066 , India . Email:

出版信息

Chem Sci. 2017 Apr 1;8(4):3026-3030. doi: 10.1039/c6sc04522g. Epub 2017 Jan 30.

DOI:10.1039/c6sc04522g
PMID:28451370
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5380879/
Abstract

An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An generated -boronic acid containing chalcone provides the chiral benzoxaboroles an asymmetric oxa-Michael addition of hydroxyl group attached to the boronic acid triggered by the cinchona alkaloid based chiral amino-squaramide catalysts. In general, good yields with good to excellent enantioselectivities (up to 99%) were obtained. The resulting benzoxaboroles were converted to the corresponding chiral β-hydroxy ketones without affecting the enantioselectivity.

摘要

已开发出一种前所未有的对映选择性合成3-取代苯并硼氧烷的方法。一种由含查耳酮的硼酸生成的中间体，在基于金鸡纳生物碱的手性氨基方酰胺催化剂引发下，通过硼酸上连接的羟基进行不对称氧杂迈克尔加成反应，从而提供手性苯并硼氧烷。一般来说，能获得良好的产率以及良好至优异的对映选择性（高达99%）。所得的苯并硼氧烷被转化为相应的手性β-羟基酮，且对映选择性不受影响。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ec1/5380879/ba4b8b70af8e/c6sc04522g-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ec1/5380879/77392d508aa4/c6sc04522g-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ec1/5380879/0e826019284a/c6sc04522g-s3.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ec1/5380879/ba4b8b70af8e/c6sc04522g-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ec1/5380879/77392d508aa4/c6sc04522g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ec1/5380879/b7bdf4b16c1c/c6sc04522g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ec1/5380879/5ed69afb989a/c6sc04522g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ec1/5380879/919eb0231f22/c6sc04522g-f2.jpg
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