The first example of magnesium carbenoid 1,3-CH insertion reaction: a novel method for synthesis of cyclopropanes from 1-chloroalkyl phenyl sulfoxides in high yields

被引：27

作者：

Satoh, T ^{[1
]}

Musashi, J ^{[1
]}

Kondo, A ^{[1
]}

机构：

[1] Sci Univ Tokyo, Dept Chem, Fac Sci, Shinjuku Ku, Tokyo 1628601, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 04期

关键词：

cyclopropane; sulfoxide; sulfoxide-magnesium exchange; magnesium carbenoid; C-H insertion;

D O I：

10.1016/j.tetlet.2004.11.146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 1-chloroalkyl phenyl sulfoxides having a geminal methyl group or a geminal benzyl group at the 2-position in THF at -78 degreesC with isopropylmagnesium chloride gave magnesium carbenoids. Carbenoid 1,3-CH insertion reaction of the magnesium carbenoids took place instantaneously to afford cyclopropanes in high to quantitative yields. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：599 / 602

页数：4

共 8 条

[1] A method for the synthesis of cyclopropanes by regiospecific and regioselective magnesium carbenoid 1,3-CH insertion as the key reactions
Watanabe, Hiroyuki
Ogata, Shingo
Satoh, Tsuyoshi
TETRAHEDRON, 2010, 66 (30) : 5675 - 5686
[2] The first example of regiospecific magnesium carbenoid 1,3-CH insertion: its mechanism and stereochemistry
Ogata, Shingo
Masaoka, Shigeyuki
Sakai, Ken
Satoh, Tsuyoshi
TETRAHEDRON LETTERS, 2007, 48 (29) : 5017 - 5021
[3] Generation of magnesium carbenoids from 1-chloroalkyl phenyl sulfoxides with a Grignard reagent and applications to alkylation and olefin synthesis
Satoh, T
Kondo, A
Musashi, J
TETRAHEDRON, 2004, 60 (25) : 5453 - 5460
[4] A versatile synthesis, including asymmetric synthesis, of bicyclo[n.1.0]alkanes from cyclic ketones via the magnesium carbenoid 1,3-CH insertion as a key reaction
Satoh, Tsuyoshi
Ogata, Shingo
Wakasugi, Daisuke
TETRAHEDRON LETTERS, 2006, 47 (40) : 7249 - 7253
[5] A synthesis of bicyclo[n.1.0]alkanes having tert-butyl carboxylate or acetamide moiety via the intramolecular 1,3-CH insertion of magnesium carbenoids
Ogata, Shingo
Saitoh, Hideki
Wakasugi, Daisuke
Satoh, Tsuyoshi
TETRAHEDRON, 2008, 64 (24) : 5711 - 5720
[6] A synthesis of di- and tri-substituted β,γ-unsaturated esters from aldehydes by the magnesium carbenoid 1,2-CH and 1,2-CC insertion as the key reaction
Yamashita, Hironori
Satoh, Tsuyoshi
TETRAHEDRON, 2009, 65 (03) : 613 - 627
[7] A new synthesis of β,γ-unsaturated esters from three components, aldehydes, chloromethyl p-tolyl sulfoxide, and tert-butyl acetate, via magnesium carbenoid 1,2-CH and 1,2-CC insertion as the key reaction
Satoh, Tsuyoshi
Yamashita, Hironori
Musashi, Jun
TETRAHEDRON LETTERS, 2007, 48 (41) : 7295 - 7300
[8] Reaction of magnesium alkylidene carbenoids with lithium α-sulfonyl carbanions:: A novel synthesis of tri- and tetra-substituted allenes from 1-chlorovinyl p-tolyl sulfoxides and sulfones
Satoh, T
Sakamoto, T
Watanabe, M
Takano, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (08) : 966 - 970

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