Enzyme-catalyzed enantioselective diaryl ketone reductions

被引：93

作者：

Truppo, Matthew D. ^{[1
]}

Pollard, David ^{[1
]}

Devine, Paul ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Sharp & Dohme Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 02期

关键词：

D O I：

10.1021/ol0627909

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of diarylmethanols via the reduction of a range of substituted benzophenone and benzoylpyridine derivatives with ketoreductase enzymes (KREDs) has afforded chiral products with high yield (> 90%) and ee (up to > 99%). Ortho, meta, and para substitutions with a variety of electron-donating, electron-withdrawing, and halogen groups were examined. Substitution at the ortho position and/or highly electronically dissymmetric molecules were not required for good selectivity, as is the case with conventional chemical catalyst reductions.

引用

页码：335 / 338

页数：4

共 23 条

[1]

BAROUH V, 1971, J MED CHEM, V14, P834

[2] Selective hydrogenation for fine chemicals: Recent trends and new developments [J].

Blaser, HU ;

Malan, C ;

Pugin, B ;

Spindler, F ;

Steiner, H ;

Studer, M .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151

[3] PREPARATIVE SYNTHESES OF OPTICALLY PURE ORTHOSUBSTITUTED BENZHYDROLS BY ASYMMETRIC REDUCTIONS OF THE CORRESPONDING BENZOPHENONES [J].

BROWN, E ;

LEZE, A ;

TOUET, J .

TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :841-844

[4] ASYMMETRIC REDUCTIONS OF KETONES USING LITHIUM ALUMINUM-HYDRIDE MODIFIED WITH N,N-DIALKYL DERIVATIVES OF (R)-(-)-2-AMINOBUTAN-1-OL [J].

BROWN, E ;

PENFORNIS, A ;

BAYMA, J ;

TOUET, J .

TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :339-342

[5] Asymmetric bioreduction of a bisaryl ketone to its corresponding (S)-bisaryl alcohol, by the yeast Rhodotorula pilimanae ATCC 32762 [J].

Chartrain, M ;

Lynch, J ;

Choi, WB ;

Churchill, H ;

Patel, S ;

Yamazaki, S ;

Volante, R ;

Greasham, R .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2000, 8 (4-6) :285-288

[6] Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction [J].

Corey, EJ ;

Helal, CJ .

TETRAHEDRON LETTERS, 1996, 37 (32) :5675-5678

[7]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

[8]

2-Z

[9] Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride [J].

Corey, EJ ;

Helal, CJ .

TETRAHEDRON LETTERS, 1996, 37 (28) :4837-4840

[10] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES [J].

COREY, EJ ;

HELAL, CJ .

TETRAHEDRON LETTERS, 1995, 36 (50) :9153-9156

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