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用于亲电五氟苯基化的空间位阻不对称二芳基-λ(3)-碘烷及一种合成具有全碳立体中心的α-五氟苯基羰基化合物的方法。

Sterically Demanding Unsymmetrical Diaryl-λ(3)-iodanes for Electrophilic Pentafluorophenylation and an Approach to α-Pentafluorophenyl Carbonyl Compounds with an All-Carbon Stereocenter.

作者信息

Matsuzaki Kohei, Okuyama Kenta, Tokunaga Etsuko, Shiro Motoo, Shibata Norio

机构信息

Department of Nanopharmaceutical Science & Department of Frontier Materials, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan) E-mail:

Rigaku Corporation 3-9-12 Mastubara-cho, Akishima, Tokyo 196-8666 (Japan).

出版信息

ChemistryOpen. 2014 Dec;3(6):233-7. doi: 10.1002/open.201402045. Epub 2014 Sep 17.

DOI:10.1002/open.201402045
PMID:25558441
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4280821/
Abstract

A sterically demanding unsymmetrical pentafluorophenyl-triisopropylphenyl-λ(3)-iodane was developed as an effective reagent for the electrophilic pentafluorophenylation of various β-keto esters and a β-keto amide. 17 examples of α-pentafluorophenylated 1,3-dicarbonyl compounds 3 having a quaternary carbon center are provided. The resulting compounds were nicely transformed into chiral α-pentafluorophenyl ketones with an all-carbon stereogenic center in high yields and high enantioselectivities using asymmetric organocatalysis (up to 98 % ee) or asymmetric metal catalysis (up to 82 % ee).

摘要

一种空间位阻较大的不对称五氟苯基-三异丙基苯基-λ(3)-碘烷被开发为一种有效的试剂，用于各种β-酮酯和β-酮酰胺的亲电五氟苯基化反应。提供了17个具有季碳中心的α-五氟苯基化1,3-二羰基化合物3的实例。使用不对称有机催化（高达98% ee）或不对称金属催化（高达82% ee），所得化合物能够以高收率和高对映选择性顺利转化为具有全碳立体中心的手性α-五氟苯基酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/cb17039ef58a/open0003-0233-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/4b263e425f9a/open0003-0233-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/bda7475ee21e/open0003-0233-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/63cdd63a13f5/open0003-0233-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/2bc0433a51d6/open0003-0233-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/cb17039ef58a/open0003-0233-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/4b263e425f9a/open0003-0233-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/bda7475ee21e/open0003-0233-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/63cdd63a13f5/open0003-0233-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/2bc0433a51d6/open0003-0233-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79a8/4280821/cb17039ef58a/open0003-0233-f5.jpg

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