TBD-catalyzed α-sulfenylation of cyclic ketones: desymmetrization of 4-substituted cyclohexanones

被引：10
|
作者：
Poladura, Belen [1 ]
Martinez-Castaneda, Angel [1 ]
Rodriguez-Solla, Humberto [1 ]
Concellon, Carmen [1 ]
del Amo, Vicente [1 ]
机构：
[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain
来源：
TETRAHEDRON | 2012年 / 68卷 / 32期
关键词：
Organocatalysis; Guanidines; Stereoselective reactions; DIRECT ALDOL REACTION; GUANIDINES; EPOXIDES; THIOLS;
D O I：
10.1016/j.tet.2012.05.124
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A low loading of triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzes the alpha-sulfenylation reaction of ketones employing tetramethylthiuram disulfide (TMTDS) as electrophilic reagent. This methodology is mild, effective and straightforward, rendering the desired products in high yield. Prochiral 4-substituted cyclohexanones can be desymmetrized with remarkable diastereoselectivity following this protocol. The dithiocarbamoyl function was shown to be easily removed upon reduction, affording thiols (1-mercaptan-2-ols). (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6438 / 6446
页数：9
相关论文
共 50 条
  • [21] Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides
    Toriyama, M
    Sugasawa, K
    Shindo, M
    Tokutake, N
    Koga, K
    TETRAHEDRON LETTERS, 1997, 38 (04) : 567 - 570
  • [22] Stereoselective electrochemical transformation of 4-substituted cyclohexanones into cis-5-substituted-2,2-dimethoxycyclohexanols
    Elinson, MN
    Feducovich, SK
    Dmitriev, DE
    Dorofeev, AS
    Vereshchagin, AN
    Nikishin, GI
    TETRAHEDRON LETTERS, 2001, 42 (32) : 5557 - 5559
  • [23] SUBSTITUENT EFFECTS IN HETEROGENEOUS CATALYSIS .9. ADSORPTION STRENGTH AND REACTIVITY OF 4-SUBSTITUTED CYCLOHEXANONES IN PLATINUM-METAL-CATALYZED HYDROGENATION
    CHIHARA, T
    TANAKA, K
    JOURNAL OF CATALYSIS, 1983, 80 (01) : 97 - 105
  • [24] cis-trans selectivity of enzyme-catalyzed additions to 4-substituted cyclohexanones -: Correlation with the prelog/Ringold model of enzymatic hydrogenation
    Effenberger, F
    Roos, J
    Kobler, C
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (11) : 1876 - +
  • [25] Asymmetric fluorination of 4-substituted pyrazolones catalyzed by quinine
    Bao, Xiaoze
    Wei, Shiqiang
    Zou, Liwei
    Song, Yuming
    Qu, Jingping
    Wang, Baomin
    TETRAHEDRON-ASYMMETRY, 2016, 27 (9-10) : 436 - 441
  • [26] Stereoselective electrochemical transformation of 4-substituted cyclohexanones into cis-5-substituted 2,2-dimethoxycyclohexanols
    M. N. Elinson
    S. K. Feducovich
    D. E. Dmitriev
    A. S. Dorofeev
    A. N. Vereshchagin
    G. I. Nikishin
    Russian Chemical Bulletin, 2002, 51 : 1478 - 1482
  • [27] STERIC AND KINETIC EFFECTS OF CHANGING SOLVENT AND REAGENT IN GRIGNARD REACTIONS ON SOME 4-SUBSTITUTED CYCLOHEXANONES
    CIANETTI, C
    DIMAIO, G
    PIGNATELLI, V
    TAGLIATESTA, P
    VECCHI, E
    ZEULI, E
    TETRAHEDRON, 1983, 39 (04) : 657 - 666
  • [28] REINVESTIGATION ON THE OPTICAL PURITIES OF OPTICALLY-ACTIVE TRIMETHYLSILYL ENOL ETHERS OF 4-SUBSTITUTED CYCLOHEXANONES
    AOKI, K
    NAKAJIMA, M
    TOMIOKA, K
    KOGA, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1993, 41 (05) : 994 - 996
  • [29] Dehydrogenative coupling of 4-substituted Pyridines catalyzed by diruthenium complexes
    Kawashima, Takashi
    Takao, Toshiro
    Suzuki, Hiroharu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) : 11006 - +
  • [30] Asymmetric Wittig reaction of chiral arsonium ylides .1. Asymmetric olefination of 4-substituted cyclohexanones
    Dai, WM
    Wu, JL
    Huang, X
    TETRAHEDRON-ASYMMETRY, 1997, 8 (12) : 1979 - 1982
12345