1,6-ASYMMETRIC INDUCTION IN LEWIS-ACID PROMOTED REACTIONS OF EPSILON-METHOXY-ALLYLSTANNANES AND EPSILON-HYDROXY-ALLYLSTANNANES AND ALDEHYDES

被引：39

作者：

CAREY, JS ^{[1
]}

THOMAS, EJ ^{[1
]}

机构：

[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(00)79268-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylstannanes with an epsilon-methoxy or epsilon-hydroxy substituent undergo reactions with aldehydes promoted by tin(IV)bromide to give syn-1,6-diol derivatives with useful regio- and stereo-selectivity.

引用

页码：3935 / 3938

页数：4

共 10 条

[1] 1,5-ASYMMETRIC INDUCTION IN REACTIONS BETWEEN (ALKOXYALLYL)STANNANES AND ALDEHYDES - INFLUENCE OF THE LEWIS-ACID AND O-SUBSTITUENT [J].

CAREY, JS ;

COULTER, TS ;

THOMAS, EJ .

TETRAHEDRON LETTERS, 1993, 34 (24) :3933-3934

[2] SYNTHESIS OF OPTICALLY-ACTIVE (E)-1-ALKOXYMETHOXYBUT-2-ENYL(TRIBUTYL)STANNANES - STEREOCHEMISTRY OF THEIR THERMAL-REACTIONS WITH ALDEHYDES [J].

JEPHCOTE, VJ ;

PRATT, AJ ;

THOMAS, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1529-1535

[3] SYNTHESIS OF (+/-)-10,22-DIOXOKOPSANE AND (+/-)-KOPSANONE, HEPTACYCLIC INDOLE ALKALOIDS - SYNTHETIC AND MECHANISTIC STUDIES [J].

MAGNUS, P ;

GALLAGHER, T ;

BROWN, P ;

HUFFMAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (07) :2105-2114

[4] 1,5-ASYMMETRIC INDUCTION IN REACTIONS BETWEEN DELTA-ALKOXYALLYLSTANNANES AND ALDEHYDES INDUCED BY TIN (IV) CHLORIDE [J].

MCNEILL, AH ;

THOMAS, EJ .

TETRAHEDRON LETTERS, 1990, 31 (43) :6239-6242

[5] 1,5-ASYMMETRIC INDUCTION IN REACTIONS OF DELTA-ALKOXYALLYL-STANNANES - STEREOSELECTIVE REACTIONS WITH CHIRAL ALDEHYDES [J].

MCNEILL, AH ;

THOMAS, EJ .

TETRAHEDRON LETTERS, 1992, 33 (10) :1369-1372

[6]

MCNEILL AH, 1992, SYNLETT, P585

[7] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[8]

Pereyre M., 1987, TIN ORGANIC SYNTHESI

[9]

PRTT AJ, 1989, J CHEM SOC P1, P1521

[10] ON THE USE OF THE O-METHYLMANDELATE ESTER FOR ESTABLISHMENT OF ABSOLUTE-CONFIGURATION OF SECONDARY ALCOHOLS [J].

TROST, BM ;

BELLETIRE, JL ;

GODLESKI, S ;

MCDOUGAL, PG ;

BALKOVEC, JM ;

BALDWIN, JJ ;

CHRISTY, ME ;

PONTICELLO, GS ;

VARGA, SL ;

SPRINGER, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2370-2374

← 1 →