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

共 50 条

[41] Alkynyl-functionalised and linked bicyclo[1.1.1]pentanes of group 14
Augenstein, Timo
A-Burgos, Pascual On
Nied, Dominik
Breher, Frank
CHEMICAL COMMUNICATIONS, 2012, 48 (54) : 6803 - 6805
[42] SYNTHESIS OF 1-ALKYNYLBICYCLO[1.1.1]PENTANES
BUNZ, U
SZEIMIES, G
TETRAHEDRON LETTERS, 1989, 30 (16) : 2087 - 2088
[43] Direct Diazoarylation of [1.1.1]Propellane with Arenediazonium Salts: A Modular Assembly of Arylated Diazo Bicyclo[1.1.1]pentanes
Nan, Hailing
Cheng, Beiyi
Zhang, Duo
Wang, Kaiping
Wang, Shuli
Xu, Bingxin
Zhang, Shuwei
Koenig, Burkhard
Zhang, Guodong
ORGANIC LETTERS, 2024, 26 (39) : 8424 - 8429
[44] Synthesis of bridgehead-substituted bicyclo[1.1.1]pentanes - A review (vol 28, pg 411, 1996)
Della, EW
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (06) : U1 - &
[45] Symmetric bridgehead-to-bridgehead coupling of bicyclo[1.1.1]pentanes and [n]staffanes
Mazal, C
Paraskos, AJ
Michl, J
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07): : 2116 - 2119
[46] Catalytic undirected borylation of tertiary C–H bonds in bicyclo[1.1.1]pentanes and bicyclo[2.1.1]hexanes
Isaac F. Yu
Jenna L. Manske
Alejandro Diéguez-Vázquez
Antonio Misale
Alexander E. Pashenko
Pavel K. Mykhailiuk
Sergey V. Ryabukhin
Dmitriy M. Volochnyuk
John F. Hartwig
Nature Chemistry, 2023, 15 : 685 - 693
[47] POLAR SUBSTITUENT EFFECTS IN 1,3-DISUBSTITUTED BICYCLO[1.1.1]PENTANES
APPLEQUIST, DE
RENKEN, TL
WHEELER, JW
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25): : 4985 - 4995
[48] Multicomponent Radical Cross-Coupling Reaction of [1.1.1]Propellane: Synthesis of 1-Arylthiol-3-Heteroaryl Bicyclo[1.1.1]pentanes &DAG;
Li, Lin
Liu, Yumiao
Li, Jian
Chen, Qing
Zhang, Pengfei
Shen, Jiabin
Wu, Jirong
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (18) : 3112 - 3117
[49] Enantioselective synthesis of 2-substituted bicyclo[1.1.1]pentanes via sequential asymmetric imine addition of bicyclo[1.1.0]butanes and skeletal editing
Che, Jin-Teng
Ding, Wei-Yi
Zhang, Hong-Bo
Wang, Yong-Bin
Xiang, Shao-Hua
Tan, Bin
NATURE CHEMISTRY, 2025, 17 (03) : 393 - 402
[50] Synthesis of gem-Diboromethyl-Substituted Bicyclo[1.1.1]pentanes and Their Application in Palladium-Catalyzed Cross Couplings
Ma, Xiaoshen
Jiang, Yuan
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (03): : 1665 - 1694

← 1 2 3 4 5 →