Synthesis of Enantioenriched α-Chiral Bicyclo[1.1.1]pentanes

被引：42

作者：

Wong, Marie L. J. ^{[1
]}

Mousseau, James J. ^{[2
]}

Mansfield, Steven J. ^{[1
]}

Anderson, Edward A. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England

[2] Pfizer Worldwide Res & Dev, Eastern Point Rd, Groton, CT 06340 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

BIOLOGICAL EVALUATION; BRIDGEHEAD; DESIGN; DERIVATIVES; FLUORINE; POTENT; SCOPE;

D O I：

10.1021/acs.orglett.9b00691

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclo[1.1.1]pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficient route to alpha-chiral BCPs, via highly diastereoselective asymmetric enolate functionalization. We also describe the application of this chemistry to the synthesis of BCP analogues of phenylglycine and tarenflurbil, the single enantiomer of the NSAID flurbiprofen.

引用

页码：2408 / 2411

页数：4

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