Asymmetric synthesis of diarylmethylamines: preparation of selective opioid delta receptor ligands

被引:40
作者
Delorme, D [1 ]
Berthelette, C [1 ]
Lavoie, R [1 ]
Roberts, E [1 ]
机构
[1] Astra Res Ctr Montreal, Dept Med Chem, St Laurent, PQ H4S 1Z9, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/S0957-4166(98)00419-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two different methods were used for the construction of optically active diarylmethylamines. Diastereoselective alkylation on an aldimine/oxazolidine 2a/2b derived from (R)/(S)phenylglycinol or enantioselective reduction of 4-[eta(6)-chromium tricarbonylbenzoyl] bromobenzene using chiral oxazoborolidine followed by amine introduction to furnish optically active diarylmethylamines. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3963 / 3966
页数:4
相关论文
共 15 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   AN EFFICIENT SYNTHESIS OF THE BENZHYDRYLPIPERAZINE DELTA-OPIOID AGONIST (+)-BW373U86 [J].
BISHOP, MJ ;
MCNUTT, RW .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (12) :1311-1314
[3]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[4]   Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride [J].
Corey, EJ ;
Helal, CJ .
TETRAHEDRON LETTERS, 1996, 37 (28) :4837-4840
[5]   REACTIONS OF CARBONYL-COMPOUNDS WITH GRIGNARD-REAGENTS IN THE PRESENCE OF CERIUM CHLORIDE [J].
IMAMOTO, T ;
TAKIYAMA, N ;
NAKAMURA, K ;
HATAJIMA, T ;
KAMIYA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4392-4398
[6]   A SIMPLE AND EFFECTIVE ENANTIOMERIC SYNTHESIS OF A CHIRAL PRIMARY AMINE [J].
MIAO, CK ;
SORCEK, R ;
JONES, PJ .
TETRAHEDRON LETTERS, 1993, 34 (14) :2259-2262
[7]   LEAD-TETRAACETATE CLEAVAGE OF CHIRAL PHENYLGLYCINOL DERIVED SECONDARY-AMINES WITHOUT RACEMIZATION [J].
MOKHALLALATI, MK ;
PRIDGEN, LN .
SYNTHETIC COMMUNICATIONS, 1993, 23 (14) :2055-2064
[8]  
OPALKA CJ, 1995, SYNTHESIS-STUTTGART, P766
[9]   1,2-ADDITION VS 1,4-ADDITION OF NUCLEOPHILIC ORGANOMETALLICS TO NONRACEMIC 2-(1-NAPHTHYL)-1,3-OXAZOLIDINES AND 2-CINNAMYL-1,3-OXAZOLIDINES [J].
PRIDGEN, LN ;
MOKHALLALATI, MK ;
WU, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1237-1241
[10]   ADDITION OF ARYLLITHIUM COMPOUNDS TO OXIME ETHERS [J].
RODRIQUES, KE ;
BASHA, A ;
SUMMERS, JB ;
BROOKS, DW .
TETRAHEDRON LETTERS, 1988, 29 (28) :3455-3458