A new method for the synthesis of α-thio aldehydes and alcohols from aldehydes with one-carbon elongation

被引：15

作者：

Satoh, T ^{[1
]}

Kubota, K ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(00)00087-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step and high-yield method for the synthesis of alpha-thio aldehydes from aldehydes with one-carbon elongation is realized by using chloromethyl phenyl sulfoxide as a one-carbon homologating agent. The alpha-thio aldehydes are easily converted to desulfurized alcohols with Bu3SnH and AIBN in refluxing benzene in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2121 / 2124

页数：4

共 20 条

[1] TRI-NORMAL-BUTYLTIN HYDRIDE - A SELECTIVE REDUCING AGENT FOR 1,3-DITHIOLANES [J].

GUTIERREZ, CG ;

STRINGHAM, RA ;

NITASAKA, T ;

GLASSCOCK, KG .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (17) :3393-3395

[2]

Hase, 1987, UMPOLED SYNTHONS

[3] NEW HORIZONS IN CARBONYL CHEMISTRY - REAGENTS FOR NUCLEOPHILIC ACYLATION [J].

LEVER, OW .

TETRAHEDRON, 1976, 32 (16) :1943-1971

[4] REACTION OF SULFONIUM SALTS OF FORMALDEHYDE DITHIOACETALS WITH AROMATIC-ALDEHYDES [J].

MAKOSZA, M ;

SYPNIEWSKI, M .

TETRAHEDRON LETTERS, 1994, 35 (33) :6141-6142

[5]

MARTIN SF, 1979, SYNTHESIS-STUTTGART, P633

[6] A NEW STRATEGY FOR 1,4-POLYCARBONYL AND 1,4,7-POLYCARBONYL COMPOUNDS [J].

SATO, T ;

OKAZAKI, H ;

OTERA, J ;

NOZAKI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) :5209-5211

[7] LIGAND-EXCHANGE REACTION OF SULFOXIDES IN ORGANIC-SYNTHESIS - A NEW SYNTHESIS OF ALPHA-CHLOROKETONES FROM CARBONYL-COMPOUNDS WITH ONE-CARBON HOMOLOGATION [J].

SATOH, T ;

MIZU, Y ;

KAWASHIMA, T ;

YAMAKAWA, K .

TETRAHEDRON, 1995, 51 (03) :703-710

[8] NEW METHOD FOR GENERATION OF BETA-OXIDO CARBENOID VIA LIGAND-EXCHANGE REACTION OF SULFOXIDES - A VERSATILE PROCEDURE FOR ONE-CARBON HOMOLOGATION OF CARBONYL-COMPOUNDS [J].

SATOH, T ;

ITOH, N ;

GENGYO, K ;

TAKADA, S ;

ASAKAWA, N ;

YAMANI, Y ;

YAMAKAWA, K .

TETRAHEDRON, 1994, 50 (41) :11839-11852

[9] GENERATION OF THE ALPHA-SULFINYL CARBENOID FROM ALPHA-CHLORO SULFOXIDES - A NEW METHOD FOR ONE-CARBON HOMOLOGATION OF KETONES TO ALPHA-SULFINYL KETONES [J].

SATOH, T ;

HAYASHI, Y ;

MIZU, Y ;

YAMAKAWA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (05) :1412-1418

[10] One-carbon ring enlargement of lactones [J].

Satoh, T ;

Kurihara, T .

TETRAHEDRON LETTERS, 1998, 39 (50) :9215-9218

← 1 2 →