SN1 reactions with planar chiral (arene)Cr(CO)3-Substituted α-propargyl cations -: Regio- and diastereoselective additions to novel ambident electrophiles

被引：26

作者：

Müller, TJJ ^{[1
]}

Netz, A ^{[1
]}

机构：

[1] Univ Munich, Inst Organ Chem, D-81377 Munich, Germany

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(99)00450-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Planar chiral ortho substituted (arene)Cr(CO)(3)-stabilized alpha-propargylic cations 4 react in a S(N)l fashion with sulfur, nitrogen and pi-nucleophiles to give regioselectively the corresponding propargyl derivatives 5 in good yields and excellent diastereoselectivities (d.r. > 9:1). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3145 / 3148

页数：4

共 22 条

[1]

Ansorge M, 1999, EUR J INORG CHEM, P225

[2] STEREOSELECTIVE ALKYNYLATION OF CHIRAL BENZALDEHYDE CHROMIUM TRICARBONYL COMPLEXES - SYNTHESIS OF OPTICALLY-ACTIVE ALKYNYL ALCOHOLS [J].

BALDOLI, C ;

DELBUTTERO, P ;

LICANDRO, E ;

MAIORANA, S ;

PAPAGNI, A ;

TORCHIO, M .

TETRAHEDRON LETTERS, 1993, 34 (49) :7943-7946

[3]

CAFFYN AJM, 1995, COMPREHENSIVE ORGANO, V12, P685

[4]

Capon B.M., 1976, Neighboring Group Participation

[5]

CAREY FA, 1990, ADV ORGANIC CHEM, V1

[6] Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride [J].

Corey, EJ ;

Helal, CJ .

TETRAHEDRON LETTERS, 1996, 37 (28) :4837-4840

[7] RELATIVE REACTIVITIES OF ALKYL CHLORIDES UNDER FRIEDEL-CRAFTS CONDITIONS [J].

DAUSCHMIDT, JP ;

MAYR, H .

CHEMISCHE BERICHTE, 1994, 127 (01) :205-212

[8]

DAVIES SG, 1993, SYNLETT, P323

[9]

HAYNES L, 1975, CARBONIUM IONS, V5

[10] THE EFFECT OF TRANSITION-METAL BENZYL AND PROPARGYL SPECIES ON THE BEHAVIOR OF STEROIDAL HORMONES [J].

JAOUEN, G .

PURE AND APPLIED CHEMISTRY, 1986, 58 (04) :597-616

← 1 2 3 →