Asymmetric synthesis of cis-5-substituted pyrrolidine 2-phosphonates using metal carbenoid NH insertion and β-amino β-ketophosphonates

被引：53

作者：

Davis, FA ^{[1
]}

Wu, YZ ^{[1
]}

Xu, H ^{[1
]}

Zhang, JY ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 24期

关键词：

D O I：

10.1021/ol048157+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cis-5-substituted pyrrolidine phosphonates, proline surrogates, are prepared by a highly stereoselective intramolecular metal carbenoid N-H insertion from a sulfinimine-derived delta-amino alpha-diazo beta-ketophosphonate.

引用

页码：4523 / 4525

页数：3

共 31 条

[1]

Davies H.M. L., 1991, ORG SYNTH, V70, P93

[2] Asymmetric synthesis of (+)-preussin from N-sulfinyl δ-amino β-ketoesters [J].

Davis, FA ;

Deng, JH .

TETRAHEDRON, 2004, 60 (23) :5111-5115

[3] Asymmetric synthesis of cyclic α-amino phosphonates using masked oxo sulfinimines (N-sulfinyl imines) [J].

Davis, FA ;

Lee, SH ;

Xu, H .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3774-3781

[4] Asymmetric synthesis of the carbocyclic nucleoside building block (R)-(+)-4-aminocyclopentenone using δ-amino β-ketophosphonates and ring-closing metathesis (RCM) [J].

Davis, FA ;

Wu, YZ .

ORGANIC LETTERS, 2004, 6 (08) :1269-1272

[5] Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2,4,6-trimethylphenylsulfinamide [J].

Davis, FA ;

Ramachandar, T ;

Wu, YZ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6894-6898

[6] Sulfinimine-mediated asymmetric synthesis of β-hydroxy α-amino phosphonates [J].

Davis, FA ;

Prasad, KR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7249-7253

[7] Asymmetric synthesis of cis-5-tert-butylproline with metal carbenoid NH insertion [J].

Davis, FA ;

Yang, B ;

Deng, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5147-5152

[8] Asymmetric synthesis of aziridine 2-phosphonates from enantiopure sulfinimines (N-sulfinyl imines).: Synthesis of α-amino phosphonates [J].

Davis, FA ;

Wu, YZ ;

Yan, HX ;

McCoull, W ;

Prasad, KR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2410-2419

[9] 2H-azirine 3-phosphonates:: A new class of chiral iminodienophiles.: Asymmetric synthesis of quaternary piperidine phosphonates [J].

Davis, FA ;

Wu, YZ ;

Yan, HX ;

Prasad, KR ;

McCoull, W .

ORGANIC LETTERS, 2002, 4 (04) :655-658

[10] Asymmetric synthesis of substituted prolines from δ-amino β-ketoesters.: Methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate [J].

Davis, FA ;

Fang, TN ;

Goswami, R .

ORGANIC LETTERS, 2002, 4 (09) :1599-1602

← 1 2 3 4 →