Efficient syntheses of secondary and tertiary 2-aryl- and 2-heteroaryl-allyl alcohols

被引：6

作者：

Katritzky, AR ^{[1
]}

Toader, D ^{[1
]}

Wang, XJ ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 26期

关键词：

D O I：

10.1021/jo980840k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of alpha-aryl-, alpha-heteroaryl-, and alpha-heteroatom-substituted masked alkenyllithiums with aldehydes and ketones provide a general method for the synthesis of allylic alcohols substituted with an aryl or heteroaryl in the beta position and aryl, heteroaryl or alkyl substituents in the a position via a [1,4]-C-->O silicon rearrangement. In the case of reactions with enolizable aldehydes and ketones, anhydrous CeCl3 was used as an additive. High diastereoselectivities are observed for allyl alcohols produced from a-substituted aldehydes.

引用

页码：9978 / 9982

页数：5

共 40 条

[1]

Brook A.G., 1980, REARRANGEMENTS GROUN, V2, P149

[2] Selective reduction of alpha,beta-unsaturated aldehydes and ketones to allylic alcohols with diisobutylalkoxyalanes [J].

Cha, JS ;

Kwon, OO ;

Kwon, SY .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (03) :355-359

[3] Anhydrous cerium(III) chloride - Effect of the drying process on activity and efficiency [J].

Dimitrov, V ;

Kostova, K ;

Genov, M .

TETRAHEDRON LETTERS, 1996, 37 (37) :6787-6790

[4] ALLYLIC SULFOXIDES - USEFUL INTERMEDIATES IN ORGANIC SYNTHESIS [J].

EVANS, DA ;

ANDREWS, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (05) :147-155

[5] The presence of water in the common CeCl3/RLi alkylation system [J].

Evans, WJ ;

Feldman, JD ;

Ziller, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (19) :4581-4584

[6]

FUJII A, 1995, SYNTHESIS-STUTTGART, P78

[7] Simple one-pot transformations of toluene-p-sulfonates of 2,3-epoxy alcohols into allylic alcohols [J].

Fujii, N ;

Habashita, H ;

Akaji, M ;

Nakai, K ;

Ibuka, T ;

Fujiwara, M ;

Tamamura, H ;

Yamamoto, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (09) :865-866

[8] AMINOBOROHYDRIDES .2. REGIOSPECIFIC REDUCTIONS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH LITHIUM PYRROLIDINOBOROHYDRIDE - A FACILE CONVERSION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES TO THE CORRESPONDING ALLYLIC ALCOHOLS IN HIGH-PURITY [J].

FULLER, JC ;

STANGELAND, EL ;

GORALSKI, CT ;

SINGARAM, B .

TETRAHEDRON LETTERS, 1993, 34 (02) :257-260

[9]

Godleslcy S., 1991, COMPREHENSIVE ORGANI, V4, P585

[10] A NOVEL SYNTHESIS OF HOMOLOGATED ALLYLIC ALCOHOLS USING DIMETHYLSULFONIUM METHYLIDE [J].

HARNETT, JJ ;

ALCARAZ, L ;

MIOSKOWSKI, C ;

MARTEL, JP ;

LEGALL, T ;

SHIN, DS ;

FALCK, JR .

TETRAHEDRON LETTERS, 1994, 35 (13) :2009-2012

← 1 2 3 4 →