ALLYLIC ALCOHOLS OF UNEXPECTED CONFIGURATION BY OXAZABOROLIDINE-CATALYZED REDUCTION OF ALPHA,BETA-UNSATURATED KETONES - AN EXPLANATION-BASED ON MO CALCULATIONS

被引：29

作者：

BACH, J ^{[1
]}

BERENGUER, R ^{[1
]}

FARRAS, J ^{[1
]}

GARCIA, J ^{[1
]}

MESEGUER, J ^{[1
]}

VILARRASA, J ^{[1
]}

机构：

[1] UNIV BARCELONA,DEPT QUIM ORGAN,DIV 3,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 11期

关键词：

D O I：

10.1016/0957-4166(95)00357-U

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

While the reduction of most alpha,beta-unsaturated ketones with BH3:SMe(2) in the presence of (R)B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine [(R)-2] affords allylic alcohols of the S configuration, that of alpha,beta-unsaturated ketones branched at both the alpha and alpha' positions gives alcohols of the R configuration. Theoretical calculations on complexes of representative enones with BH3 (6-31G*) or with BH3:(R)-2 (AMI) may account for the apparent changes in the steric requirements on either side of the CO group.

引用

页码：2683 / 2686

页数：4

共 41 条

[1] Oxazaborolidine-catalyzed enantioselective reduction of α-methylene ketones to allylic alcohols
Matsuo, Jun-ichi
Kozai, Takaaki
Nishikawa, Osamu
Hattori, Yu
Ishibashi, Hiroyuki
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6902 - 6904
[2] Selective reduction of alpha,beta-unsaturated aldehydes and ketones to allylic alcohols with diisobutylalkoxyalanes
Cha, JS
Kwon, OO
Kwon, SY
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (03) : 355 - 359
[3] SELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES TO ALLYLIC ALCOHOLS WITH DIISOBUTYLCHLOROALANE
CHA, JS
KWON, OO
KWON, SY
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1995, 16 (11) : 1009 - 1011
[4] A MEERWEIN - PONNDORF - VERLEY TYPE REDUCTION OF ALPHA,BETA-UNSATURATED KETONES TO ALLYLIC ALCOHOLS CATALYZED BY MGO
KASPAR, J
TROVARELLI, A
LENARDA, M
GRAZIANI, M
TETRAHEDRON LETTERS, 1989, 30 (20) : 2705 - 2706
[5] Asymmetric hydrogenation of cyclic alpha,beta-unsaturated ketones to chiral allylic alcohols
Ohkuma, T
Ikehira, H
Ikariya, T
Noyori, R
SYNLETT, 1997, (05) : 467 - +
[6] RUTHENIUM-CATALYZED ALLYLATION OF PRIMARY ALCOHOLS BY ALLYLIC ACETATES - A NOVEL SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES
KONDO, T
MUKAI, T
WATANABE, Y
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02): : 487 - 489
[7] SYNTHESIS OF DIACIDS AND KETO ACIDS BY RUTHENIUM TETRAOXIDE CATALYZED OXIDATION OF CYCLIC ALLYLIC ALCOHOLS AND ALPHA,BETA-UNSATURATED KETONES
WEBSTER, FX
RIVASENTERRIOS, J
SILVERSTEIN, RM
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04): : 689 - 691
[8] HYDROGENATION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES TO THE UNSATURATED ALCOHOLS CATALYZED BY HYDRIDOIRIDIUM PHOSPHINE COMPLEXES
FARNETTI, E
PESCE, M
KASPAR, J
SPOGLIARICH, R
GRAZIANI, M
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) : 746 - 747
[9] The mechanism of oxidation of allylic alcohols to alpha,beta-unsaturated ketones by cytochrome p450
Bellucci, G
Chiappe, C
Pucci, L
Gervasi, PG
CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (05) : 871 - 874
[10] STEREOSELECTIVE SYNTHESIS OF ALLYLIC ALCOHOLS VIA THE REDUCTION OF ALPHA,BETA-UNSATURATED EPOXIDES WITH DIBORANE
ZAIDLEWICZ, M
UZAREWICZ, A
SARNOWSKI, R
SYNTHESIS-STUTTGART, 1979, (01): : 62 - 64

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