1,3-ASYMMETRIC INDUCTION IN THE REDUCTION OF ALPHA-ALKYL BETA-KETOSULFOXIDES WITH DIBAL/ZNBR2

被引：0

作者：

BARROS, D ^{[1
]}

CARRENO, MC ^{[1
]}

RUANO, JLG ^{[1
]}

MAESTRO, MC ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,FAC CIENCIAS,DEPT QUIM CI,CANTOBLANCO,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 19期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly stereoselective reduction of chiral alpha-alkyl beta-ketosulfoxides with DIBAL/ZnBr2 is governed by the configuration at the sulfur (1-3-induction) and not by that of the C-alpha (1,2-induction) as it has been previously reported. This fact considerably increases the scope of the Solladie's methodology to synthesize optically pure secondary carbinols. Those substituents decreasing the capability of the carbonyl oxygen to chelate the ZnBr2 induce a decrease in the stereoselectivity.

引用

页码：2733 / 2736

页数：4

共 50 条

[21] 1,3-ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS VIA 2,5-TRANS DISUBSTITUTED IMIDAZOLIDIN-4-ONES
AMOROSO, R
CARDILLO, G
TOMASINI, C
TETRAHEDRON LETTERS, 1991, 32 (17) : 1971 - 1974
[22] Substrate-directed diastereoselective hydroformylations, 2 1,3-asymmetric induction in stereoselective rhodium-catalyzed hydroformylation of homomethallylic alcohols
Breit, B
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (06) : 1123 - 1134
[23] 1,3-ASYMMETRIC INDUCTION IN THE ALDOL ADDITION-REACTIONS OF METHYL KETONE ENOLATES AND ENOLSILANES TO BETA-SUBSTITUTED ALDEHYDES - A MODEL FOR CHIRALITY TRANSFER
EVANS, DA
DUFFY, JL
DART, MJ
TETRAHEDRON LETTERS, 1994, 35 (46) : 8537 - 8540
[24] 1,3-ASYMMETRIC INDUCTION IN ADDITION-REACTIONS OF CHIRAL BETA-ALKOXY ALDEHYDES - EFFICIENT CHELATION CONTROL VIA LEWIS ACIDIC TITANIUM REAGENTS
REETZ, MT
JUNG, A
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) : 4833 - 4835
[25] 1,3-asymmetric induction in the intramolecular [2+2] cycloaddition of alkene-keteniminium salts. Synthesis of (+)-gibberellic acid key intermediate
Shim, PJ
Kim, HD
TETRAHEDRON LETTERS, 1998, 39 (51) : 9517 - 9520
[26] 1,3-ASYMMETRIC INDUCTION - HIGHLY STEREOSELECTIVE SYNTHESIS OF 2,4-TRANS-DISUBSTITUTED GAMMA-BUTYROLACTONES AND GAMMA-BUTYROTHIOLACTONES
TAMARU, Y
MIZUTANI, M
FURUKAWA, Y
KAWAMURA, SI
YOSHIDA, ZI
YANAGI, K
MINOBE, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) : 1079 - 1085
[27] ASYMMETRIC MICROBIAL REDUCTION OF ETHYL AND ISOPROPYL-ALPHA,1,3-TRIOXO-2-ISOINDOLINEBUTYRATE
MATZINGER, PK
WIRZ, B
LEUENBERGER, HGW
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1990, 32 (05) : 533 - 537
[28] SYNTHESES VIA ISOXAZOLINES .5. 1,3-ASYMMETRIC INDUCTION IN THE REDUCTION OF 3,5-DISUBSTITUTED 2-ISOXAZOLINES - DIASTEREOSELECTIVE SYNTHESIS AND CONFIGURATIONAL ASSIGNMENT OF GAMMA-AMINO ALCOHOLS
JAGER, V
BUSS, V
LIEBIGS ANNALEN DER CHEMIE, 1980, (01): : 101 - 121
[29] Chelation-controlled 1,3-asymmetric induction in the radical addition-allylation reactions of 4-hydroxy- and 4-alkoxy-2-methylenecarboxylic esters
Nagano, H
Hirasawa, T
Yajima, T
SYNLETT, 2000, (07) : 1073 - 1075
[30] STEREOCHEMISTRY OF ADDITION TO CARBONYL GROUP .10. ASYMMETRIC INDUCTION IN REDUCTION OF 1-PHENYL-2-ALKYL-1-PROPANONES
FERNANDEZGONZALEZ, F
PEREZOSSORIO, R
PLUMET, J
ANALES DE QUIMICA, 1975, 71 (02): : 208 - 212

← 1 2 3 4 5 →