Site and stereoselectivity of the cyclopropanation of unsymmetrically substituted 1,3-dienes by the Simmons-Smith reaction.

被引：4

作者：

Guerreiro, MC

Schuchardt, U

机构：

[1] Instituto de Química, Universidade Estadual de Campinas, 13083-970 - Campinas, SP

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 09期

关键词：

D O I：

10.1080/00397919608002620

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the Simmons-Smith reaction, 1,3-dienes are preferentially cyclopropanated at the more electron-rich double bond to afford the trans-vinylcyclopropane; an allylic hydroxyl group increases the reactivity and directs the cyclopropanation to the adjacent double bond.

引用

页码：1793 / 1800

页数：8

共 13 条

[1] BERTRAND M, 1967, B SOC CHIM FR, P3549
[2] BUCHEL KH, 1962, Z NATURFORSCH PT B, VB 17, P349
[3] NEW STEREOSPECIFIC SYNTHETIC ROUTES TO TRISUBSTITUTED OLEFINS
COREY, EJ
YAMAMOTO, H
HERRON, DK
ACHIWA, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (22) : 6635 - &
[4] Doyle M.P., 1986, CATALYSIS ORGANIC RE, P47
[5] REACTION OF METHYLENE WITH BUTA-1,3-DIENE
GRZYBOWSKA, B
TROTMANDICKENSO.AF
KNOX, JH
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1961, (OCT): : 4402 - +
[6] GUERREIRO MC, 1993, THESIS U ESTADUAL CA
[7] REPLACEMENT OF CARBONYL OXYGEN OF HYDROXY KETONES BY METHYLENE AND 1,1-ETHANO GROUPS BY REACTION WITH SIMMONS-SMITH REAGENT
HARRISON, IT
RAWSON, RJ
TURNBULL, P
FRIED, JH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) : 3515 - &
[8] CYCLOPROPYL CONJUGATION IN OLEFINIC ESTERS . CONFORMATIONAL EFFECTS ON ULTRAVIOLET ABSORPTION
JORGENSON, MJ
LEUNG, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (14) : 3769 - +
[9] UBER PROTONENKATALYSIERTE REAKTIONEN AN STEROID-CYCLOPROPYLALKOHOLEN
LAURENT, H
MULLER, H
WIECHERT, R
[J]. CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (12): : 3836 - &
[10] MONOMERS AND POLYMERS, A SYNTHESIS OF VINYL CYCLOPROPANE AND DICYCLOPROPYL
OVERBERGER, CG
HALEK, GW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (03) : 867 - &

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