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 [J].

Mikolajczyk, M ;

Lyzwa, P ;

Drabowicz, 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 [J].

Mikolajczyk, M ;

Lyzwa, P ;

Drabowicz, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (24) :3991-3994

[23] Preparation of chiral α-diazophosphonic acid derivatives [J].

Moody, CJ ;

Morfitt, CN ;

Slawin, AMZ .

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 [J].

Nakamura, E ;

Yoshikai, N ;

Yamanaka, M .

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 [J].

Nakamura, Y ;

Ukita, T .

ORGANIC LETTERS, 2002, 4 (14) :2317-2320

[26] HOMOGENEOUS CATALYSIS IN DECOMPOSITION OF DIAZO COMPOUNDS BY COPPER CHELATES [J].

NOZAKI, H ;

TAKAYA, H ;

MORIUTI, S ;

NOYORI, R .

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 [J].

Palacios, F ;

de Retana, AMO ;

de Marigorta, EM ;

Rodriguez, M ;

Pagalday, J .

TETRAHEDRON, 2003, 59 (15) :2617-2623

[28] Bioactive natural products with carbon-phosphorus bonds and their biosynthesis [J].

Seto, H ;

Kuzuyama, T .

NATURAL PRODUCT REPORTS, 1999, 16 (05) :589-596

[29] Predicting the diastereoselectivity of Rh-mediated intramolecular C-H insertion [J].

Taber, DF ;

You, KK ;

Rheingold, AL .

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 [J].

Taber, DF ;

Malcolm, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3717-3721

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