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

[21] A new efficient procedure for asymmetric synthesis of α-aminophosphonic acids via addition of lithiated bis(diethylamino)phosphine borane complex to enantiopure sulfinimines
Mikolajczyk, M
Lyzwa, P
Drabowicz, J
[J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (23) : 2571 - 2576
[22] Asymmetric addition of dialkyl phosphite and diamido phosphite anions to chiral, enantiopure sulfinimines:: a new, convenient route to enantiomeric α-aminophosphonic acids
Mikolajczyk, M
Lyzwa, P
Drabowicz, J
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (24) : 3991 - 3994
[23] Preparation of chiral α-diazophosphonic acid derivatives
Moody, CJ
Morfitt, CN
Slawin, AMZ
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (11) : 1657 - 1661
[24] Mechanism of C-H bond activation/C-C bond formation reaction between diazo compound and alkane catalyzed by dirhodium tetracarboxylate
Nakamura, E
Yoshikai, N
Yamanaka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) : 7181 - 7192
[25] Construction of heterocyclic compounds by use of α-diazophosphonates:: New one-pot syntheses of indoles and isocoumarins
Nakamura, Y
Ukita, T
[J]. ORGANIC LETTERS, 2002, 4 (14) : 2317 - 2320
[26] HOMOGENEOUS CATALYSIS IN DECOMPOSITION OF DIAZO COMPOUNDS BY COPPER CHELATES
NOZAKI, H
TAKAYA, H
MORIUTI, S
NOYORI, R
[J]. TETRAHEDRON, 1968, 24 (09) : 3655 - &
[27] Aza-Wittig reaction of N-phosphorylalkyl phosphazenes with carbonyl compounds and phenylisocyanate.: Synthesis of 4-amino-3-phosphoryl-2-azadienes and pyrazine-phosphonates
Palacios, F
de Retana, AMO
de Marigorta, EM
Rodriguez, M
Pagalday, J
[J]. TETRAHEDRON, 2003, 59 (15) : 2617 - 2623
[28] Bioactive natural products with carbon-phosphorus bonds and their biosynthesis
Seto, H
Kuzuyama, T
[J]. NATURAL PRODUCT REPORTS, 1999, 16 (05) : 589 - 596
[29] Predicting the diastereoselectivity of Rh-mediated intramolecular C-H insertion
Taber, DF
You, KK
Rheingold, AL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (03) : 547 - 556
[30] Rhodium-mediated intramolecular C-H insertion: Probing the geometry of the transition state
Taber, DF
Malcolm, SC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) : 3717 - 3721

← 1 2 3 4 →