AMINOBOROHYDRIDES .6. DIASTEREOSELECTIVE REDUCTION OF THE CARBON-NITROGEN DOUBLE-BOND IN CHIRAL IMINES USING LITHIUM DIETHYLAMINOBOROHYDRIDE AND LITHIUM DIISOPROPYLAMINOBOROHYDRIDE

被引：20

作者：

FULLER, JC ^{[1
]}

BELISLE, CM ^{[1
]}

GORALSKI, CT ^{[1
]}

SINGARAM, B ^{[1
]}

机构：

[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)73507-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium aminoborohydrides (LAB), obtained by the reaction of n-BuLi with amine-boranes, readily reduce imines to the corresponding secondary amines. Lithium diethylaminoborohydride [Li(Et)(2)NBH3] and lithium diisopropylaminoborohydride [Li(i-Pr)(2)NBH3] reduce chiral aliphatic and aromatic imines, derived from alpha-methylbenzylamines, to give the corresponding enantiomerically enriched secondary amines. The yields of secondary amines from this procedure range from very good to essentially quantitative. The diastereomeric induction in the, eduction of the carbon-nitrogen double bond with Li(Et)(2)NBH3 and Li(i-Pr)(2)NBH3 ranged from moderate to very good.

引用

页码：5389 / 5392

页数：4

共 36 条

[1] REDUCTION OF SCHIFF BASES .2. BENZHYDRYLAMINES AND STRUCTURALLY RELATED COMPOUNDS [J].

BILLMAN, JH ;

TAI, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (04) :535-539

[2] LITHIUM CYANOHYDRIDOBORATE A VERSATILE NEW REAGENT [J].

BORCH, RF ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (14) :3996-&

[3] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].

BORCH, RF ;

BERNSTEIN, MD ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+

[4]

CHARLES JP, 1970, B SOC CHIM FR, P4439

[5] STUDIES ON ASYMMETRIC SYNTHESIS OF ALPHA-AMINO ACIDS .2. NEW SYSTEMS FOR HIGHLY SPECIFIC ASYMMETRIC SYNTHESIS WITH CONSERVATION OF CHIRAL REAGENT [J].

COREY, EJ ;

SACHDEV, HS ;

GOUGOUTAS, JZ ;

SAENGER, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2488-+

[6]

DEMAILLY G, 1975, TETRAHEDRON LETT, P2471

[7] DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL SECONDARY-AMINES WITH 2 CHIRAL CENTERS DIRECTLY ATTACHED TO THE NITROGEN ATOM [J].

ELEVELD, MB ;

HOGEVEEN, H ;

SCHUDDE, EP .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3635-3642

[8]

FIAUD JC, 1977, TETRAHEDRON LETT, P1019

[9] SYNTHESIS AND CHARACTERIZATION OF LITHIUM AMINOBOROHYDRIDES - A NEW CLASS OF POWERFUL REDUCING AGENTS [J].

FISHER, GB ;

HARRISON, J ;

FULLER, JC ;

GORALSKI, CT ;

SINGARAM, B .

TETRAHEDRON LETTERS, 1992, 33 (32) :4533-4536

[10] AMINOBOROHYDRIDES .3. A FACILE REDUCTION OF TERTIARY AMIDES TO THE CORRESPONDING AMINES AND ALCOHOLS IN HIGH-PURITY USING LITHIUM AMINOBOROHYDRIDES - STERICALLY CONTROLLED SELECTIVE C-N OR C-O BOND-CLEAVAGE [J].

FISHER, GB ;

FULLER, JC ;

HARRISON, J ;

GORALSKI, CT ;

SINGARAM, B .

TETRAHEDRON LETTERS, 1993, 34 (07) :1091-1094

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