Highly enantio- and diastereoselective tandem generation of cyclopropyl alcohols with up to four contiguous stereocenters

被引：76

作者：

Kim, HY ^{[1
]}

Lurain, AE ^{[1
]}

García-García, P ^{[1
]}

Carroll, PJ ^{[1
]}

Walsh, PJ ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 38期

关键词：

D O I：

10.1021/ja0539239

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Three highly enantio- and diastereoselective one-pot procedures for the synthesis of cyclopropyl and iodocyclopropyl alcohols with up to four contiguous stereocenters are reported. Route 1 involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective cyclopropanation. Route 2 parallels route 1, except that iodoform is used to generate the zinc carbenoid, and the products are iodocyclopropyl alcohols. Route 3 entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective cyclopropanation. Copyright © 2005 American Chemical Society.

引用

页码：13138 / 13139

页数：2

共 50 条

[1] ORGN 138-Highly enantio- and diastereoselective tandem generation of cyclopropyl alcohols
Kim, Hun Young
Walsh, Patrick J.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[2] Highly enantio- and diastereoselective one-pot synthesis of acyclic epoxy alcohols with three contiguous stereocenters
Lurain, AE
Maestri, A
Kelly, AR
Carroll, PJ
Walsh, PJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) : 13608 - 13609
[3] Tandem catalytic enantio- and diastereoselective synthesis of cyclopropyl alcohols using aryl aldehydes
Kim, Hun Young
Walsh, Patrick J.
[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2012, 25 (11) : 933 - 938
[4] Enantio- and diastereoselective synthesis of γ-amino alcohols
Verkade, Jorge M. M.
Quaedflieg, Peter J. L. M.
Verzijl, Gerard K. M.
Lefort, Laurent
van Delft, Floris L.
de Vries, Johannes G.
Rutjes, Floris P. J. T.
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (77) : 14462 - 14464
[5] Tandem reactions for streamlining synthesis: Enantio- and diastereoselective one-pot generation of functionalized epoxy alcohols
Hussain, Mahmud M.
Walsh, Patrick J.
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (08) : 883 - 893
[6] Highly enantio- and diastereoselective catalytic one-pot synthesis of amino cyclopropyl carbinols
Valenta, Petr
Walsh, Patrick J.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
[7] Highly Enantio- and Diastereoselective Synthesis of β-Methyl-γ-monofluoromethyl-Substituted Alcohols
Yang, Wenguo
Wei, Xinle
Pan, Yuanhang
Lee, Richmond
Zhu, Bo
Liu, Hongjun
Yan, Lin
Huang, Kuo-Wei
Jiang, Zhiyong
Tan, Choon-Hong
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (29) : 8066 - 8070
[8] Highly Enantio- and Diastereoselective One-Pot Methods for the Synthesis of Halocyclopropyl Alcohols
Kim, Hun Young
Salvi, Luca
Carroll, Patrick J.
Walsh, Patrick J.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (03) : 954 - 962
[9] Highly enantio- and diastereoselective one-pot synthesis of acyclic epoxy alcohols and allylic epoxy alcohols
Kelly, Ann Rowley
Lurain, Alice E.
Walsh, Patrick J.
[J]. Journal of the American Chemical Society, 2005, 127 (42): : 14668 - 14674
[10] Highly enantio- and diastereoselective one-pot synthesis of acyclic epoxy alcohols and allylic epoxy alcohols
Kelly, AR
Lurain, AE
Walsh, PJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (42) : 14668 - 14674

← 1 2 3 4 5 →