Synthesis of 2,3-disubstituted pyrrolidines by intramolecular addition of α-aminoalkyl radicals to electron deficient C=C bonds

被引：41

作者：

Aurrecoechea, JM ^{[1
]}

Fernández, A ^{[1
]}

Gorgojo, JM ^{[1
]}

Saornil, C ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ, E-48080 Bilbao, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 23期

关键词：

cyclization; pyrrolidines; radicals; samarium;

D O I：

10.1016/S0040-4020(99)00359-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,3-Disubstituted pyrrolidines are prepared by SmI2-pranoted cyclization of alpha-amino radicals generated from N-(alpha-benzotriazolylalkyl)alkenylamines containing a C=C bond activated by an electron withdrawing substituent. The diastereoselectivity of cyclization is moderate and depends on the nature of the substituent at the pyrrolidine 2-position. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7345 / 7362

页数：18

共 91 条

[11] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].

BECKWITH, ALJ ;

SCHIESSER, CH .

TETRAHEDRON, 1985, 41 (19) :3925-3941

[12]

BECKWITH ALJ, 1991, J ORG CHEM, V56, P5791

[13]

Bertrand MP, 1997, SYNLETT, P1420

[14] 1-aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage [J].

Bols, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :1-8

[15] SAMARIUM DIIODIDE MEDIATED ALKYLATION OF SATURATED HETEROCYCLES ALPHA TO NITROGEN [J].

BOOTH, SE ;

BENNECHE, T ;

UNDHEIM, K .

TETRAHEDRON, 1995, 51 (12) :3665-3674

[16]

BOSONE E, 1983, SYNTHESIS-STUTTGART, P942

[17] SYNTHESIS OF THE HOMOCHIRAL TRICYCLIC HEART OF MANZAMINE-A [J].

BRANDS, KMJ ;

MEEKEL, AAP ;

PANDIT, UK .

TETRAHEDRON, 1991, 47 (10-11) :2005-2026

[18] Stereoselective synthesis of polyhydroxylated indolizidines from γ-hydroxy α,β-unsaturated sulfones [J].

Carretero, JC ;

Arrayás, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2993-3005

[19] Preparation of tetrahydrofuran, gamma-lactone, chromanol and pyrrolidine systems by sequential 5-exo-digonal radical cyclization, 1,5-hydrogen transfer from silicon, and 5-endo-trigonal cyclization [J].

Clive, DLJ ;

Yang, W .

CHEMICAL COMMUNICATIONS, 1996, (14) :1605-1606

[20] REACTIONS OF PROTECTED AMINO-ACID CHLORIDES MEDIATED BY SMI2 [J].

COLLIN, J ;

NAMY, JL ;

JONES, G ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1992, 33 (21) :2973-2976

← 1 2 3 4 5 6 7 8 9 10 →