Synthesis of C2-symmetric analogues of 4-(pyrrolidino)pyridine:: new chiral nucleophilic catalysts

被引：74

作者：

Spivey, AC

Maddaford, A

Fekner, T

Redgrave, AJ

Frampton, CS

机构：

[1] Roche Discovery Welwyn, Welwyn Garden City, Herts, England

[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

[3] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 20期

关键词：

D O I：

10.1039/b004704j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of a series of enantiomerically pure C-2-symmetric 4-(pyrrolidino)pyridine (PPY) derivatives by SNAr of 4-halo-/4-phenoxypyridines and by cyclocondensation from 4-aminopyridine are described. Preliminary results pertaining to their use as catalysts for acylative kinetic resolution of 1-phenylethanol are also presented. A single-crystal X-ray analysis of PPY If is reported.

引用

页码：3460 / 3468

页数：9

共 83 条

[1] POLYHALOGENO-AROMATIC COMPOUNDS .15. PREPARATION AND REACTIONS OF TETRACHLOROPYRIDINE-4-SULPHENYL CHLORIDE AND TETRACHLOROPYRIDINE-4-SULPHONYL CHLORIDE
AGER, E
SUSCHITZ.H
IDDON, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (11): : 1530 - &
[2] ANGULO J, 1959, AN R SOC ESP FIS Q B, V55, P527
[3] *BRUK AXS, 1997, SMART SAINT SADABS A
[4] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS
BURK, MJ
FEASTER, JE
NUGENT, WA
HARLOW, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10125 - 10138
[5] *CAMBR SOFT CORP, 1997, COMP PROGR CS CHEM3D
[6] ANTITUBERCULOSIS AGENTS .3. PYRIDINE-4-SULPHON-AMIDES AND PYRIDINE-4-SULPHON-SULPHONHYDRAZIDES
COMRIE, AM
STENLAKE, JB
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1958, (OCT): : 3514 - 3518
[7] A MILD PROCEDURE FOR THE CONVERSION OF 1,2-DIOLS TO OLEFINS
COREY, EJ
HOPKINS, PB
[J]. TETRAHEDRON LETTERS, 1982, 23 (19) : 1979 - 1982
[8] POLAR INTERACTIONS BETWEEN STACKED PI-SYSTEMS IN FLUORINATED 1,8-DIARYLNAPHTHALENES - IMPORTANCE OF QUADRUPOLE-MOMENTS IN MOLECULAR RECOGNITION
COZZI, F
PONZINI, F
ANNUNZIATA, R
CINQUINI, M
SIEGEL, JS
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (09): : 1019 - 1020
[9] DEANE CC, 1969, J CHEM SOC CHEM COMM, P813
[10] ASYMMETRIC DIELS-ALDER CYCLOADDITIONS WITH C2-SYMMETRICAL CHIRAL CARBAMOYLNITROSO DIENOPHILES
DEFOIN, A
BROUILLARDPOICHET, A
STREITH, J
[J]. HELVETICA CHIMICA ACTA, 1991, 74 (01) : 103 - 109

← 1 2 3 4 5 6 7 8 9 →