First highly diastereoselective synthesis of syn α-methyl β-fluoroalkyl β-amino esters

被引：48

作者：

Fustero, S ^{[1
]}

Pina, B ^{[1
]}

de la Torre, MG ^{[1
]}

Navarro, A ^{[1
]}

de Arellano, CR ^{[1
]}

Simón, A ^{[1
]}

机构：

[1] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 07期

关键词：

D O I：

10.1021/ol990774o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new two-step approach for the diastereoselective synthesis of the syn alpha-methyl beta-fluoroalkyl beta-amino esters 4 has been developed. This approach is based on the chemical reduction of the fluorinated beta-enamino esters 3, which have been previously obtained from imidoyl chlorides 1 and lithium ester enolates, with Znl(2)/NaBH4 as the reducing agent. The process takes place with high syn diastereoselectivity and good to excellent yields. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction.

引用

页码：977 / 980

页数：4

共 41 条

[31] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS BASED ON BINAP - RUTHENIUM(II) CATALYZED HYDROGENATION
LUBELL, WD
KITAMURA, M
NOYORI, R
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (07) : 543 - 554
[32] Ojima I., 1996, ACS S SERIES, V639
[33] PETTIT GR, 1989, HETEROCYCLES, V28, P553
[34] ALPHA-ALKYLATION OF BETA-AMINOBUTANOATES WITH LK-1.2-INDUCTION
SEEBACH, D
ESTERMANN, H
[J]. TETRAHEDRON LETTERS, 1987, 28 (27) : 3103 - 3106
[35] Tandem protocol for the stereoselective synthesis of different polyfunctional β-amino acids and 3-amino-substituted carbohydrates
Sewald, N
Hiller, KD
Korner, M
Findeisen, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) : 7263 - 7274
[36] Biomimetic transamination of α-alkyl β-keto carboxylic esters.: Chemoenzymatic approach to the stereochemically defined α-alkyl β-fluoroalkyl β-amino acids
Soloshonok, VA
Soloshonok, IV
Kukhar, VP
Svedas, VK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) : 1878 - 1884
[37] Enantioselective biomimetic transamination of beta-keto carboxylic acid derivatives. An efficient asymmetric synthesis of beta-(fluoroalkyl) beta-amino acids
Soloshonok, VA
Ono, T
Soloshonok, IV
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7538 - 7539
[38] ONE-POT SYNTHESIS OF TRIFLUOROACETIMIDOYL HALIDES
TAMURA, K
MIZUKAMI, H
MAEDA, K
WATANABE, H
UNEYAMA, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) : 32 - 35
[39] A novel synthesis of β-trifluoromethyl-substituted isoserine via intramolecular rearrangement of imino ethers
Uneyama, K
Hao, JA
Amii, H
[J]. TETRAHEDRON LETTERS, 1998, 39 (23) : 4079 - 4082
[40] A computational study of charge delocalization and ring fluoro substituent effects in 4-fluoromethylphenoxides
Urban, JJ
von Tersch, RL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) : 3409 - 3416

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