Asymmetric synthesis of syn-(2R,3S)- and anti-(2S,3 s)-ethyl diamino-3-phenylpropanoates from N-(benzylidene)-p-toluenesulfinamide and glycine enolates

被引：59

作者：

Davis, FA ^{[1
]}

Deng, JH ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 16期

关键词：

D O I：

10.1021/ol048981y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-alpha,beta-diamino esters with high diastereoselectivities and good yields.

引用

页码：2789 / 2792

页数：4

共 35 条

[1] Catalytic asymmetric Mannich reactions of glycine derivatives with imines.: A new approach to optically active α,β-diamino acid derivatives
Bernardi, L
Gothelf, AS
Hazell, RG
Jorgensen, KA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) : 2583 - 2591
[2] Sulfinimines of trifluoropyruvate:: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids
Bravo, P
Crucianelli, M
Vergani, B
Zanda, M
[J]. TETRAHEDRON LETTERS, 1998, 39 (42) : 7771 - 7774
[3] Asymmetric synthesis of anti-(2S,3S)- and syn-(2R,3S)-diaminobutanoic acid
Bunnage, ME
Burke, AJ
Davies, SG
Millican, NL
Nicholson, RL
Roberts, PM
Smith, AD
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (21) : 3708 - 3715
[4] Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2,4,6-trimethylphenylsulfinamide
Davis, FA
Ramachandar, T
Wu, YZ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) : 6894 - 6898
[5] Asymmetric synthesis of aziridine 2-phosphonates from enantiopure sulfinimines (N-sulfinyl imines).: Synthesis of α-amino phosphonates
Davis, FA
Wu, YZ
Yan, HX
McCoull, W
Prasad, KR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) : 2410 - 2419
[6] Improved synthesis of enantiopure sulfinimines (thiooxime S-oxides) from p-toluenesulfinamide and aldehydes and ketones
Davis, FA
Zhang, YL
Andemichael, Y
Fang, TA
Fanelli, DL
Zhang, HM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) : 1403 - 1406
[7] Asymmetric synthesis of aziridine 2-phosphonates and azirinyl phosphonates from enantiopure sulfinimines
Davis, FA
McCoull, W
[J]. TETRAHEDRON LETTERS, 1999, 40 (02) : 249 - 252
[8] Asymmetric synthesis of α-methylphosphophenylalanine derivatives using sulfinimine-derived enantiopure aziridine-2-phosphonates
Davis, FA
McCoull, W
Titus, DD
[J]. ORGANIC LETTERS, 1999, 1 (07) : 1053 - 1055
[9] Concise asymmetric synthesis of α-amino acid derivatives from N-sulfinylimino esters
Davis, FA
McCoull, W
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) : 3396 - 3397
[10] Davis FA, 1998, CHEM SOC REV, V27, P13

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