Highly enantioselective synthesis of α-alkyl-alanines via the catalytic phase-transfer alkylation of 2-naphthyl aldimine tert-butyl ester by using O(9)-allyl-N(1)-2′,3′,4′-trifluorobenzylhydro-cinchonidinium bromide

被引：52

作者：

Jew, SS ^{[1
]}

Jeong, BS

Lee, JH

Yoo, MS

Lee, YJ

Park, BS

Kim, MG

Park, HG

机构：

[1] Seoul Natl Univ, Pharmaceut Sci Res Inst, Seoul 151742, South Korea

[2] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 11期

关键词：

D O I：

10.1021/jo034006t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Systematic investigations to develop an efficient enantioselective synthetic method for alpha-alkyl-alanine by catalytic phase-transfer alkylation were performed. The alkylation of 2-naphthyl aldimine tert-butyl ester, 1E, with RbOH and O(9)-allyl-N-2',3',4'-trifluorobenzylhydrocinchonidinium bromide, 6, at -35degreesC showed the highest enantioselectivities, up to 96% ee.

引用

页码：4514 / 4516

页数：3

共 41 条

[1] Synthesis and biological properties of new constrained CCK-B antagonists: Discrimination of two affinity states of the CCK-B receptor on transfected CHO cells [J].

Bellier, B ;

McCortTranchepain, I ;

Ducos, B ;

Danascimento, S ;

Meudal, H ;

Noble, F ;

Garbay, C ;

Roques, BP .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (24) :3947-3956

[2] Asymmetric PTC C-alkylation mediated by TADDOL -: novel route to enantiomerically enriched α-alkyl-α-amino acids [J].

Belokon, YN ;

Kochetkov, KA ;

Churkina, TD ;

Ikonnikov, NS ;

Chesnokov, AA ;

Larionov, OV ;

Parmár, VS ;

Kumar, R ;

Kagan, HB .

TETRAHEDRON-ASYMMETRY, 1998, 9 (05) :851-857

[3] Chiral salen-metal complexes as novel catalysts for asymmetric phase transfer alkylations [J].

Belokon, YN ;

North, M ;

Kublitski, VS ;

Ikonnikov, NS ;

Krasik, PE ;

Maleev, VI .

TETRAHEDRON LETTERS, 1999, 40 (33) :6105-6108

[4]

Benedetti E, 1995, J Pept Sci, V1, P349, DOI 10.1002/psc.310010602

[5]

Benedetti E, 1996, BIOPOLYMERS, V40, P3, DOI 10.1002/(SICI)1097-0282(1996)40:1<3::AID-BIP2>3.0.CO

[6]

2-#

[7] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].

Cativiela, C ;

Diaz-de-Villegas, MD .

TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599

[8] 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

[9]

Dery O, 1996, BIOPOLYMERS, V39, P67, DOI 10.1002/(SICI)1097-0282(199607)39:1<67::AID-BIP7>3.0.CO

[10]

2-T

← 1 2 3 4 5 →