A practical synthesis of (R)- and (S)-3-amino-3,4-dihydro-1-H-quinolin-2-one

被引:16
作者
Hulin, B [1 ]
Lopaze, MG [1 ]
机构
[1] Pfizer Global Res & Dev, Groton, CT 06340 USA
关键词
D O I
10.1016/j.tetasy.2004.05.013
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric alkylation of N-(diphenylmethylene)glycine tert-butyl ester with 2-nitrobenzyl bromide followed by reductive cyclization provides (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one in high yield and high enantiomeric excess. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:1957 / 1958
页数:2
相关论文
共 14 条
[1]   Chiral salen-metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions [J].
Belokon, YN ;
North, M ;
Churkina, TD ;
Ikonnikov, NS ;
Maleev, VI .
TETRAHEDRON, 2001, 57 (13) :2491-2498
[2]  
Birch A., 2003, [No title captured], Patent No. [WO03074532 A1, 03074532]
[3]   Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst [J].
Corey, EJ ;
Noe, MC ;
Xu, F .
TETRAHEDRON LETTERS, 1998, 39 (30) :5347-5350
[4]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415
[5]   PREPARATION AND ANTIMICROBIAL PROPERTIES OF D AND L FORMS OF 3-AMINO-3,4-DIHYDRO-1-HYDROXYCARBOSTYRIL [J].
DAVIS, AL ;
BLACK, JL ;
SMITH, DR ;
FOYT, DC ;
MCCORD, TJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (03) :325-&
[6]   A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of alpha-amino acids [J].
Lygo, B ;
Wainwright, PG .
TETRAHEDRON LETTERS, 1997, 38 (49) :8595-8598
[7]   Pd-catalyzed asymmetric allylic alkylation of glycine imino ester using a chiral phase-transfer catalyst [J].
Nakoji, M ;
Kanayama, T ;
Okino, T ;
Takemoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7418-7423
[8]   Practical catalytic enantioselective synthesis of α,α-dialkyl-α-amino acids by chiral phase-transfer catalysis [J].
Ooi, T ;
Takeuchi, M ;
Kameda, M ;
Maruoka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) :5228-5229
[9]   Trimeric Cinchona alkaloid phase-transfer catalyst:: α,α′,α"-tris[O(9)-allylcinchonidinium]mesitylene tribromide [J].
Park, HG ;
Jeong, BS ;
Yoo, MS ;
Park, MK ;
Huh, H ;
Jew, SS .
TETRAHEDRON LETTERS, 2001, 42 (28) :4645-4648
[10]   Synthesis of the selective D-2 receptor agonist PNU-95666E from D-phenylalanine using a sequential oxidative cyclization strategy [J].
Romero, AG ;
Darlington, WH ;
McMillan, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6582-6587