Asymmetric reductive cyclization using the intramolecular conjugate addition of enolates onto α,β-unsaturated sulfoxides

被引:19
作者
Yoshizaki, H [1 ]
Tanaka, T [1 ]
Yoshii, E [1 ]
Koizumi, T [1 ]
Takeda, K [1 ]
机构
[1] Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Toyama 9300194, Japan
关键词
D O I
10.1016/S0040-4039(97)10414-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Li(sec-Bu)(3)BH-mediated reductive cyclization of optically pure 8-((S)-p-tolylsulfinyl)(2E,7Z)-octadienoate 9 and 7-(p-tolylsulfinyl)-2,6-heptadienoate 16 afforded trans-2-((p-tolylsulfinyl)methyl)cyclohexane-l-carboxylate and trans-2-(p-tolylsulfinyl)methyl)cyclopentane-1-carboxylate, respectively, as a single isomer. (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:47 / 50
页数:4
相关论文
共 11 条
[1]   TOTAL SYNTHESIS OF TETRONOMYCIN [J].
HORI, K ;
HIKAGE, N ;
INAGAKI, A ;
MORI, S ;
NOMURA, K ;
YOSHII, E .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2888-2902
[2]   ORGANIC-SYNTHESIS UTILIZING CHIRAL SULFOXIDES [J].
KOIZUMI, T .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1986, 44 (06) :576-590
[3]   SIMPLE AND STEREOCONTROLLED PREPARATION OF OPTICALLY PURE (E)-1-ALKENYL PARA-TOLYL AND (Z)-1-ALKENYL PARA-TOLYL SULFOXIDES VIA 1-ALKYNYL PARA-TOLYL SULFOXIDES [J].
KOSUGI, H ;
KITAOKA, M ;
TAGAMI, K ;
TAKAHASHI, A ;
UDA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1078-1082
[4]  
Perlmutter P., 1992, CONJUGATE ADDITION R
[5]   ASYMMETRIC MICHAEL ADDITIONS OF ESTER ENOLATES TO ENANTIOMERICALLY PURE VINYLIC SULFOXIDES - SYNTHESIS OF 3-SUBSTITUTED GLUTARATE ESTERS IN HIGH ENANTIOMERIC PURITY [J].
POSNER, GH ;
WEITZBERG, M ;
HAMILL, TG ;
ASIRVATHAM, E ;
HE, CH ;
CLARDY, J .
TETRAHEDRON, 1986, 42 (11) :2919-2929
[6]   ASYMMETRIC-SYNTHESIS OF CARBON CARBON BONDS USING SULFINYL CYCLOALKENONES, ALKENOLIDES, AND PYRONES [J].
POSNER, GH .
ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (02) :72-78
[7]  
Schmalz H.-G., 1991, COMPREHENSIVE ORGANI, V4, P199
[8]  
Seyden-Penne J., 2015, CHIRAL AUXILIARIES L, DOI [10.1002/(SICI)1099-0739(199705)11:5%3c457::AID-AOC568%3e3.0.CO
[9]  
2-L, DOI 10.1002/(SICI)1099-0739(199705)11:5%3C457::AID-AOC568%3E3.0.CO
[10]  
2-L]