Highly diastereoselective nucleophilic addition of organometallic reagents to 2-pyrrolidinyl nitrones: a semiempirical approach

被引：26

作者：

Merino, P ^{[1
]}

Franco, S ^{[1
]}

Gascon, JM ^{[1
]}

Merchan, FL ^{[1
]}

Tejero, T ^{[1
]}

机构：

[1] Univ Zaragoza, Fac Ciencias, ICMA, Dept Quim Organ, E-50009 Aragon, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(99)00203-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

2-Pyrrolidinyl nitrones 1 and 2 derived from L-proline and trans-4-hydroxy-L-proline, respectively, undergo nucleophilic additions of Grignard reagents and organolithium compounds with high syn selectivity, to yield enantiomerically pure pyrrolidinyl benzyl hydroxylamines. A rationale for the observed stereoselectivity based on semiempirical calculations is presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1867 / 1871

页数：5

共 13 条

[1] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[2]

DHAVALE DD, 1992, LIEBIGS ANN CHEM, P1289

[3] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[4] Synthesis and iodocyclization of homoallylic hydroxylamines [J].

Fiumana, A ;

Lombardo, M ;

Trombini, C .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5623-5626

[5]

LANTOS I, 1995, CHEM TODAY SEP, P39

[6] A NEW ROUTE TO 3,5-DISUBSTITUTED ISOXAZOLIDINES VIA THE IODOCYCLIZATION OF HOMOALLYLIC HYDROXYLAMINES [J].

MANCINI, F ;

PIAZZA, MG ;

TROMBINI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4246-4252

[7] Diastereoselective additions of organolithium and organomagnesium reagents to the C=N bond of a chiral, cyclic nitrone derived from erythrulose [J].

Marco, JA ;

Carda, M ;

Murga, J ;

Portolés, R ;

Falomir, E ;

Lex, J .

TETRAHEDRON LETTERS, 1998, 39 (20) :3237-3240

[8] Asymmetric synthesis of an isoxazolidine nucleoside analog of thymine polyoxin C [J].

Merino, P ;

Franco, S ;

Merchan, FL ;

Tejero, T .

TETRAHEDRON LETTERS, 1998, 39 (35) :6411-6414

[9]

Merino P, 1998, RRD SYNTH ORG CHEM, V1, P109

[10] Asymmetric addition reactions of lithium (trimethylsilyl) acetylide with chiral α-amino nitrones.: Synthesis of diastereomerically pure N-hydroxy-α-amino acids [J].

Merino, P ;

Franco, S ;

Merchan, FL ;

Tejero, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5627-5630

← 1 2 →