The oxazaborolidine-borane reduction of ketones: Identification and reactivity of transient intermediates

被引：34

作者：

Douglas, AW

Tschaen, DM

Reamer, RA

Shi, YJ

机构：

[1] Department of Process Research, Merck Research Laboratories, Rahway, NJ 07065

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 05期

关键词：

D O I：

10.1016/0957-4166(96)00147-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An investigation of the reaction pathway for oxazaborolidine-borane reduction of ketones has revealed a transient intermediate which can competitively reduce ketones. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1303 / 1308

页数：6

共 23 条

[1] SIMPLIFIED C-13 SPECTRAL ASSIGNMENTS USING A GRAPHICAL METHOD TO PRESENT C-13 SPECTRA RECORDED UNDER CONDITIONS OF PROTON OFF-RESONANCE SPIN DECOUPLING
BIRDSALL, B
BIRDSALL, NJ
FEENEY, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (06) : 316 - &
[2] EFFECTS OF TRIETHYLAMINE IN ASYMMETRIC REDUCTION USING OXAZABOROLIDINE REAGENTS
CAI, DW
TSCHAEN, D
SHI, YJ
VERHOEVEN, TR
REAMER, RA
DOUGLAS, AW
[J]. TETRAHEDRON LETTERS, 1993, 34 (20) : 3243 - 3246
[3] A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS
COREY, EJ
BAKSHI, RK
[J]. TETRAHEDRON LETTERS, 1990, 31 (05) : 611 - 614
[4] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS
COREY, EJ
BAKSHI, RK
SHIBATA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5551 - 5553
[5] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES
COREY, EJ
BAKSHI, RK
SHIBATA, S
CHEN, CP
SINGH, VK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) : 7925 - 7926
[6] ASYMMETRIC BORON-CATALYZED REACTIONS
DELOUX, L
SREBNIK, M
[J]. CHEMICAL REVIEWS, 1993, 93 (02) : 763 - 784
[7] NITROALKENE INTER [4+2] INTRA [3+2] TANDEM CYCLOADDITIONS .7. APPLICATION OF (R)-(-)-2,2-DIPHENYLCYCLOPENTANOL AS THE CHIRAL AUXILIARY
DENMARK, SE
SCHNUTE, ME
MARCIN, LR
THORARENSEN, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) : 3205 - 3220
[8] CATALYTIC BEHAVIOR OF OPTICALLY-ACTIVE AMINO ALCOHOL-BORANE COMPLEX IN THE ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE OXIME O-ALKYL ETHERS
ITSUNO, S
SAKURAI, Y
ITO, K
HIRAO, A
NAKAHAMA, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (01) : 395 - 396
[9] ORIGINS OF THE ENANTIOSELECTIVITY OBSERVED IN OXAZABOROLIDINE-CATALYZED REDUCTIONS OF KETONES
JONES, DK
LIOTTA, DC
SHINKAI, I
MATHRE, DJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) : 799 - 801
[10] A PRACTICAL PROCESS FOR THE PREPARATION OF TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C]-[1,3,2]OXAZABOROLE BORANE - A HIGHLY ENANTIOSELECTIVE STOICHIOMETRIC AND CATALYTIC REDUCING AGENT
MATHRE, DJ
THOMPSON, AS
DOUGLAS, AW
HOOGSTEEN, K
CARROLL, JD
CORLEY, EG
GRABOWSKI, EJJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) : 2880 - 2888

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