Asymmetric transfer hydrogenation of benzaldehydes

被引：110

作者：

Yamada, I

Noyori, R ^{[1
]}

机构：

[1] Nagoya Univ, Dept Chem, Nagoya, Aichi 4648602, Japan

[2] Nagoya Univ, Math Sci Res Ctr, Nagoya, Aichi 4648602, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 22期

关键词：

D O I：

10.1021/ol0002119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A combined system of RuCl[(R,R)-YCH(C6H5)CH(C6H5)NH2](eta (6)-arene) (Y = NSO2C6H4-4-CH3 or O) and t-C4H9OK catalyzes the asymmetric transfer hydrogenation of various benzaldehyde-1-d derivatives with 2-propanol to yield (R)-benzyl-1-d alcohols in 95-99% ee and with >99% isotopic purity. Reaction of benzaldehydes with a DCO2D-triethylamine mixture and the R,R catalyst affords the S deuterated alcohols in 97-99% ee.

引用

收藏

页码：3425 / 3427

页数：3

相关论文

共 29 条

[1] THE OXIDATION POTENTIALS OF ALDEHYDES AND KETONES [J].

ADKINS, H ;

ELOFSON, RM ;

ROSSOW, AG ;

ROBINSON, CC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (11) :3622-3629

[2] Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones: Mechanism and origin of enantioselectivity [J].

Alonso, DA ;

Brandt, P ;

Nordin, SJM ;

Andersson, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9580-9588

[3]

Arigoni D., 1969, TOPICS STEREOCHEMIST, V4, P127, DOI DOI 10.1002/9780470147139.CH4

[4] A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS AND DEUTERATED PRIMARY ALCOHOLS BY CARBONYL REDUCTION [J].

COREY, EJ ;

LINK, JO .

TETRAHEDRON LETTERS, 1989, 30 (46) :6275-6278

[5] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[6]

Doucet H, 1998, ANGEW CHEM INT EDIT, V37, P1703, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO

[7]

2-I

[8] CHIRAL METHYL-GROUPS - SMALL IS BEAUTIFUL [J].

FLOSS, HG ;

LEE, SS .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (03) :116-122

[9] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].

Fujii, A ;

Hashiguchi, S ;

Uematsu, N ;

Ikariya, T ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522

[10] The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones [J].

Haack, KJ ;

Hashiguchi, S ;

Fujii, A ;

Ikariya, T ;

Noyori, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :285-288