Stereoselective hydrogen bromide-promoted hydrogenation of an α-hydroxyoxime

被引：13

作者：

Davies, IW ^{[1
]}

Taylor, M ^{[1
]}

Marcoux, JF ^{[1
]}

Matty, L ^{[1
]}

Wu, J ^{[1
]}

Hughes, D ^{[1
]}

Reider, PJ ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)01404-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrogen bromide has been demonstrated to provide optimal cis-selectivity in the reduction of 4-chromanone alpha-hydroxyoxime (25:1 cis/trans) in 94% yield. This reaction is pivotal in the synthesis of cis-aminochromanol. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：8021 / 8025

页数：5

相关论文

共 15 条

[1] A conformational toolbox of oxazoline ligands. [J].

Davies, IW ;

Gerena, L ;

Cai, DW ;

Larsen, RD ;

Verhoeven, TR ;

Reider, PJ .

TETRAHEDRON LETTERS, 1997, 38 (07) :1145-1148

[2]

Davies IW, 1996, CHEM IND-LONDON, P412

[3] STEREOSELECTIVE REDUCTION OF ALPHA-HYDROXY OXIME ETHERS - A CONVENIENT ROUTE TO CIS-1,2-AMINO ALCOHOLS [J].

GHOSH, AK ;

MCKEE, SP ;

SANDERS, WM .

TETRAHEDRON LETTERS, 1991, 32 (06) :711-714

[4] THE ENANTIOFACE-DIFFERENTIATING (ASYMMETRIC) HYDROGENATION OF THE C=O DOUBLE-BOND WITH MODIFIED RANEY-NICKEL .36. THE DEVELOPMENT OF MODIFIED NICKEL-CATALYSTS WITH HIGH ENANTIOFACE-DIFFERENTIATING ABILITIES [J].

HARADA, T ;

YAMAMOTO, M ;

ONAKA, S ;

IMAIDA, M ;

OZAKI, H ;

TAI, A ;

IZUMI, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (08) :2323-2329

[5] AZODIFORMATE ADDUCT OF INDENE AND STEREOCHEMISTRY OF SOME 1,2-DISUBSTITUTED INDANS [J].

HUEBNER, CF ;

DONOGHUE, EM ;

NOVAK, CJ ;

DORFMAN, L ;

WENKERT, E .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (04) :1149-+

[6] SYNTHESIS OF [1]BENZOPYRANO[3,4-B][1,4]OXAZINES AS POTENTIAL ANTIDEPRESSANTS [J].

JULIAN, DR ;

MATUSIAK, ZS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (06) :1179-1182

[7] A practical synthesis of (1S,2R)-1-amimo-2-indanol, a key component of an HIV protease inhibitor, indinavir [J].

Kajiro, H ;

Mitamura, S ;

Mori, A ;

Hiyama, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1999, 72 (05) :1093-1100

[8]

Kajiro H, 1998, SYNLETT, P51

[9] ENANTIOSELECTIVE EPOXIDATION OF CONJUGATED DIENES AND ENYNES - TRANS-EPOXIDES FROM CIS-OLEFINS [J].

LEE, NH ;

JACOBSEN, EN .

TETRAHEDRON LETTERS, 1991, 32 (45) :6533-6536

[10] DIRECT ALPHA-HYDROXYLATION OF KETONES USING IODOSOBENZENE [J].

MORIARTY, RM ;

HU, H ;

GUPTA, SC .

TETRAHEDRON LETTERS, 1981, 22 (14) :1283-1286