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
Davis, FA
Deng, JH
[J]. TETRAHEDRON, 2004, 60 (23) : 5111 - 5115
[3] Asymmetric synthesis of cyclic α-amino phosphonates using masked oxo sulfinimines (N-sulfinyl imines)
Davis, FA
Lee, SH
Xu, H
[J]. 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)
Davis, FA
Wu, YZ
[J]. ORGANIC LETTERS, 2004, 6 (08) : 1269 - 1272
[5] 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
[6] Sulfinimine-mediated asymmetric synthesis of β-hydroxy α-amino phosphonates
Davis, FA
Prasad, KR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) : 7249 - 7253
[7] Asymmetric synthesis of cis-5-tert-butylproline with metal carbenoid NH insertion
Davis, FA
Yang, B
Deng, JH
[J]. 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
Davis, FA
Wu, YZ
Yan, HX
McCoull, W
Prasad, KR
[J]. 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
Davis, FA
Wu, YZ
Yan, HX
Prasad, KR
McCoull, W
[J]. 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
Davis, FA
Fang, TN
Goswami, R
[J]. ORGANIC LETTERS, 2002, 4 (09) : 1599 - 1602

← 1 2 3 4 →