A novel synthesis of carboxylic acid derivatives having a quaternary carbon at 3-position and functional groups at 4-position from 1-chlorovinyl p-tolyl sulfoxides and acetic acid esters

被引：15

作者：

Satoh, T ^{[1
]}

Sugiyama, S ^{[1
]}

Ota, H ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 16期

关键词：

carboxylic acid; spiro-lactone; quaternary carbon; sulfoxide; 1-chlorovinyl aryl sulfoxide;

D O I：

10.1016/S0040-4039(02)00414-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of the lithium enolate of acetic acid esters to 1-chlorovinyl p-tolyl sulfoxides, which were derived from ketones and chloromethyl p-tolyl sulfoxide in three steps in good yields. gave carboxylic acid esters having a quaternary carbon at the 3-position, and chlorine and sulfinyl groups at the 4-position in high yields. Various kinds of functionalized carboxylic acid derivatives, including spiro-lactones, were derived from the adducts in good to high yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3033 / 3036

页数：4

共 17 条

[1] Conjugate addition of lithium ester enolates to 1-chlorovinyl p-tolyl sulfoxides:: a novel synthesis of functionalized esters and lactones having a tertiary or a quaternary carbon at the β-position
Satoh, T
Sugiyama, S
Kamide, Y
Ota, H
TETRAHEDRON, 2003, 59 (24) : 4327 - 4336
[2] An asymmetric synthesis of carboxylic acid derivatives, including lactic acid and α-amino acid derivatives, from optically active 1-chlorovinyl p-tolyl sulfoxides and ester lithium enolates with creation of chirality at the α-position
Kido, Masahiro
Sugiyama, Shimpei
Satoh, Tsuyoshi
TETRAHEDRON-ASYMMETRY, 2007, 18 (16) : 1934 - 1947
[3] Efficient Synthesis of Cyclopropanecarboxylic Acid Esters Starting from the Conjugate Addition of Lithium Ester Enolates to 1-Chlorovinyl p-Tolyl Sulfoxides
Kimura, Tsutomu
Hattori, Yoshiaki
Momochi, Hitoshi
Nakaya, Nobuhito
Satoh, Tsuyoshi
SYNLETT, 2013, 24 (04) : 483 - 486
[4] Asymmetric synthesis of both enantiomers of esters and γ-lactones from opticafly active 1-chlorovinyl p-tolyl sulfoxides and lithium ester enolates with the formation of a tertiary or a quaternary carbon stereogenic center at the β-position
Sugiyama, S
Satoh, T
TETRAHEDRON-ASYMMETRY, 2005, 16 (03) : 665 - 673
[5] An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides
Sugiyama, Shimpei
Nakaya, Nobuhito
Satoh, Tsuyoshi
TETRAHEDRON-ASYMMETRY, 2008, 19 (04) : 401 - 406
[6] Reaction of 1-chlorovinyl p-tolyl sulfoxides with carbanion of acetonitrile:: A novel synthesis of cyclopentanone derivatives with three consecutive carbon-carbon bond-formations via the enaminonitriles
Satoh, T
Ota, H
TETRAHEDRON, 2000, 56 (29) : 5113 - 5122
[7] A novel method for asymmetric synthesis of both enantiomers of α-substituted carboxylic acid derivatives from optically active 1-chlorovinyl p-tolyl sulfoxides and lithium ester enolates with 1,4-chiral induction from the sulfur chiral center
Sugiyama, S
Kido, M
Satoh, T
TETRAHEDRON LETTERS, 2005, 46 (39) : 6771 - 6775
[8] Asymmetric synthesis of 4,4-disubstituted 2-cyclopentenones from optically active 1-chlorovinyl p-tolyl sulfoxides and cyanomethyllithium with formation of a quaternary chiral center
Satoh, T
Yoshida, M
Ota, H
TETRAHEDRON LETTERS, 2001, 42 (52) : 9241 - 9244
[9] A novel synthesis of 2,4,4-trisubstituted 2-cyclopentenones by consecutive reaction of 1-chlorovinyl p-tolyl sulfoxides with acetonitrile and its homologues
Satoh, T
Wakasugi, D
TETRAHEDRON LETTERS, 2003, 44 (40) : 7517 - 7520
[10] A novel method for the asymmetric synthesis of 4,4-disubstituted 2-cyclopentenones from optically active 1-chlorovinyl p-tolyl sulfoxides and its application to the asymmetric total synthesis of (+)-α-cuparenone
Satoh, T
Yoshida, M
Takahashi, Y
Ota, H
TETRAHEDRON-ASYMMETRY, 2003, 14 (02) : 281 - 288

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