Substituent-control of stereoselectivity in the reaction of allylic tins. Anti-selective Lewis acid-promoted reaction toward aldehydes

被引：10

作者：

Nishigaichi, Y

Ishida, N

Nishida, M

Takuwa, A

机构：

[1] Department of Chemistry, Faculty of Science, Shimane University

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 21期

关键词：

D O I：

10.1016/0040-4039(96)00645-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the reaction of cis-2-alkenyltins (allylic tins) toward aldehydes, unusual anti-homoallyl alcohols were selectively obtained when the substituent at the 2-position of the alkenyltin reagent was a bulky one such as a tert-butyl or trialkylsilyl group. This reaction is assumed to proceed via the inverse antiperiplanar acyclic transition state. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

收藏

页码：3701 / 3704

页数：4

相关论文

共 17 条

[1] REMARKABLE INCREASE IN THE DIASTEREOFACIAL SELECTIVITY OF THE ADDITION OF BETA-METHYL ALPHA-(ALKOXY)ALLYLSTANNANE TO ALDEHYDES - SUBSTITUENT EFFECTS ON DIASTEREOFACIAL SELECTIVITY [J].

GUNG, BW ;

SMITH, DT ;

WOLF, MA .

TETRAHEDRON LETTERS, 1991, 32 (01) :13-16

[2] ACYCLIC STEREOSELECTION .27. SIMPLE DIASTEREOSELECTION IN THE LEWIS ACID MEDIATED REACTIONS OF ENOLSILANES WITH ALDEHYDES [J].

HEATHCOCK, CH ;

HUG, KT ;

FLIPPIN, LA .

TETRAHEDRON LETTERS, 1984, 25 (52) :5973-5976

[3] ACYCLIC STEREOSELECTION .17. SIMPLE DIASTEREOSELECTION IN THE ADDITION OF MEDIUM-CHAIN AND LONG-CHAIN NORMAL-ALKYL KETONE LITHIUM ENOLATES TO ALDEHYDES [J].

HEATHCOCK, CH ;

LAMPE, J .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4330-4337

[4] EFFECTS OF OLEFIN GEOMETRY ON THE STEREOCHEMISTRY OF LEWIS-ACID MEDIATED ADDITIONS OF CROTYLSTANNANES TO ALDEHYDES [J].

KECK, GE ;

SAVIN, KA ;

CRESSMAN, ENK ;

ABBOTT, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7889-7896

[5] STEREOSELECTIVE ACYCLIC SYNTHESIS VIA ALLYLMETALS - THREO VICINAL DIOLS FROM BOTH E-GAMMA-ALKOXYALLYLTINS AND Z-GAMMA-ALKOXYALLYLTINS AND ALDEHYDES [J].

KOREEDA, M ;

TANAKA, Y .

TETRAHEDRON LETTERS, 1987, 28 (02) :143-146

[6] SYNTHESIS OF ENANTIOENRICHED HOMOPROPARGYLIC ALCOHOLS THROUGH DIASTEREOSELECTIVE-SE' ADDITIONS OF CHIRAL ALLENYLSTANNANES TO ALDEHYDES [J].

MARSHALL, JA ;

WANG, XJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1242-1252

[7] LEWIS-ACID PROMOTED ADDITIONS OF GAMMA-ALKOXY-)CROTYLSTANNANES AND GAMMA-(SILYLOXY)CROTYLSTANNANES TO (S)-2-(BENZYLOXY) PROPANAL [J].

MARSHALL, JA ;

JABLONOWSKI, JA ;

LUKE, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7825-7832

[8] ANOMALOUS THREO-DIASTEREOSELECTIVITY IN ALLYLIC SILANE-ALDEHYDE OR STANNANE-ALDEHYDE CONDENSATION-REACTIONS - NEW INTERPRETATION OF THE ANTIPERIPLANAR VS SYNCLINAL PROBLEM ON THE TRANSITION-STATE CONFORMATIONS [J].

MIKAMI, K ;

KAWAMOTO, K ;

LOH, TP ;

NAKAI, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (17) :1161-1163

[9] AN EASY ACCESS TO STEREODEFINED 2-PENTENYLTINS BY PARTIAL HYDROGENATION OF 2,4-PENTADIENYLTINS WITH DIAZENE [J].

NISHIGAICHI, Y ;

ISHIDA, N ;

TAKUWA, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (01) :274-276

[10] REINVESTIGATION OF THE LEWIS ACID-MEDIATED REACTION OF 3-ARYL-SUBSTITUTED ALLYLTIN REAGENTS TOWARD ALDEHYDES - DIVERGENT STEREOCONTROL OF THE PRODUCT BY LEWIS-ACIDS [J].

NISHIGAICHI, Y ;

TAKUWA, A .

CHEMISTRY LETTERS, 1994, (08) :1429-1432