STEREOSELECTIVE PHOTOCYCLOADDITION OF SILYL ENOL ETHERS TO ALDEHYDES - CONFIGURATIONAL CONTROL OF 3 STEREOGENIC CENTERS IH OXETANES

被引：18

作者：

BACH, T

机构：

[1] Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Orléansring 23

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 32期

关键词：

D O I：

10.1016/S0040-4039(00)78199-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photocycloaddition of unsymmetrically substituted alkenes to an aldehyde leads to eight possible isomeric oxetanes. In sharp contrast to most other substrates, silyl-enol ethers 1 which bear a vinylic beta-substituent favor only a single stereo- and regioisomer 2 as major product of this reaction.

引用

页码：5845 / 5848

页数：4

共 23 条

[1] Arnold D. R., 1968, ADV PHOTOCHEM, V6, P301
[2] REGIOSELECTIVE CARBOHYDROXYLATION OF ENOL ETHERS BY A PHOTOCYCLOADDITION-HYDROGENATION SEQUENCE
BACH, T
[J]. TETRAHEDRON LETTERS, 1994, 35 (12) : 1855 - 1858
[3] DIASTEREOMERICALLY PURE 3-(SILYLOXY)OXETANES BY A SELECTIVE PATERNO-BUCHI REACTION
BACH, T
JODICKE, K
[J]. CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (11): : 2457 - 2466
[4] 3-TRIMETHYLSILYLOXY-OXETANES VIA A HIGHLY SELECTIVE PATERNO-BUCHI REACTION
BACH, T
[J]. TETRAHEDRON LETTERS, 1991, 32 (48) : 7037 - 7038
[5] THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY
BUSCHMANN, H
SCHARF, HD
HOFFMANN, N
ESSER, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) : 477 - 515
[6] Buschmann H., 1991, ANGEW CHEM, V103, P480
[7] Carless H. A. J., 1984, SYNTHETIC ORGANIC PH, P425
[8] OBSERVATION OF THE 1,4-BIRADICAL IN THE PATERNO-BUCHI REACTION
FREILICH, SC
PETERS, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) : 6255 - 6257
[9] PICOSECOND DYNAMICS OF THE PATERNO-BUCHI REACTION
FREILICH, SC
PETERS, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) : 3819 - 3822
[10] INTERSYSTEM CROSSING IN TRIPLET 1,4-BIRADICALS - CONFORMATIONAL MEMORY EFFECTS ON THE STEREOSELECTIVITY OF PHOTOCYCLOADDITION REACTIONS
GRIESBECK, AG
MAUDER, H
STADTMULLER, S
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (03) : 70 - 75

← 1 2 3 →