Highly diastereoselective addition of Grignard reagents to aliphatic, enolizable N-alkylketimines and 2,2-disubstituted 1,3-oxazolidines.: Asymmetric synthesis of the antidepressant cericlamine

被引：39

作者：

Steinig, AG ^{[1
]}

Spero, DM ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Med Chem, Ridgefield, CT 06877 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 07期

关键词：

D O I：

10.1021/jo982222+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Grignard reagents were added to 2,2-disubstituted 1,3-oxazolidines and enolizable ketimines prepared from hydroxyacetone and phenylglycinol derivatives, with high to excellent diastereoselectivity, to yield 2,2-disubstituted 1,2-amino alcohol derivatives. Lewis acids had considerable influence on the yield and diastereoselectivity of the addition. This method was applied to the first asymmetric synthesis of the 5-HT reuptake inhibitor Cericlamine.

引用

页码：2406 / 2410

页数：5

共 31 条

[1]

Aubard G., 1987, Eur. Pat, Patent No. 0237366

[2] ASYMMETRIC-SYNTHESIS VIA NUCLEOPHILIC-ADDITION TO ALPHA,BETA-EPOXYIMINES [J].

BERESFORD, KJM ;

HOWE, GP ;

PROCTER, G .

TETRAHEDRON LETTERS, 1992, 33 (23) :3355-3358

[3] A new magnesium-catalyzed doubly diastereoselective anti-aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity [J].

Corey, EJ ;

Li, WD ;

Reichard, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) :2330-2336

[4]

DIMSDALE MJ, 1977, Patent No. 2378746

[5] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[6] SIMPLE AND VERSATILE SYNTHESIS OF OPTICALLY-ACTIVE 1,2-AMINO ALCOHOLS BY GRIGNARD ADDITION TO N,O-DIBENZYLGLYCERALDIMINE AND N,O-LACTALDIMINE [J].

FRANZ, T ;

HEIN, M ;

VEITH, U ;

JAGER, V ;

PETERS, EM ;

PETERS, K ;

VONSCHNERING, HG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (12) :1298-1301

[7]

Franz T, 1994, ANGEW CHEM, V106, P1308

[8] NEUROPSYCHOPHARMACOLOGICAL PROFILE OF JO-1017, A NEW ANTIDEPRESSANT AND SELECTIVE SEROTONIN UPTAKE INHIBITOR [J].

GOURET, CJ ;

WETTSTEIN, JG ;

PORSOLT, RD ;

PUECH, A ;

JUNIEN, JL .

EUROPEAN JOURNAL OF PHARMACOLOGY, 1990, 183 (04) :1478-1478

[9]

GOURET CJ, 1990, ARZNEIMITTEL-FORSCH, V40-1, P633

[10] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA CHIRAL N-ALKYLIDENESULFINAMIDES [J].

HUA, DH ;

LAGNEAU, N ;

WANG, H ;

CHEN, JS .

TETRAHEDRON-ASYMMETRY, 1995, 6 (02) :349-352

← 1 2 3 4 →