Chemoenzymatic synthesis of a novel ligand for rhodium-catalysed asymmetric hydrogenation

被引：12

作者：

Adger, B

Berens, U

Griffiths, MJ

Kelly, MJ

McCague, R

Miller, JA

Palmer, CF

Roberts, SM

Selke, R

Vitinius, U

Ward, G

机构：

[1] UNIV LIVERPOOL,DEPT CHEM,LIVERPOOL L69 7ZD,MERSEYSIDE,ENGLAND

[2] CHIROSCI PLC,CAMBRIDGE CB4 4WE,ENGLAND

[3] UNIV EXETER,DEPT CHEM,EXETER EX4 4QD,DEVON,ENGLAND

[4] UNIV ROSTOCK,MAX PLANCK GESELL FORDERUNG WISSENSCH EV,D-18055 ROSTOCK,GERMANY

来源：

CHEMICAL COMMUNICATIONS | 1997年 / 18期

关键词：

D O I：

10.1039/a704136e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The hydrogenation of alkenes 7a-g using a chiral rhodium catalyst 6 (based on a bicyclo[3.2.0]heptane framework) takes place to give the phenylalanine derivatives 8a-g with remarkably high stereoselectivity (59-92% ee).

引用

页码：1713 / 1714

页数：2

共 15 条

[1] Enantioselective catalytic hydrogenation [J].

Albrecht, J ;

Nagel, U .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :407-409

[2] A convenient asymmetric synthesis of alpha-1-arylalkylamines through the enantioselective hydrogenation of enamides [J].

Burk, MJ ;

Wang, YM ;

Lee, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5142-5143

[3] ENZYMATIC RESOLUTION OF STERICALLY DEMANDING BICYCLO[3.2.0]HEPTANES - EVIDENCE FOR A NOVEL HYDROLASE IN CRUDE PORCINE PANCREATIC LIPASE AND THE ADVANTAGES OF USING ORGANIC MEDIA FOR SOME OF THE BIOTRANSFORMATIONS [J].

COTTERILL, IC ;

SUTHERLAND, AG ;

ROBERTS, SM ;

GROBBAUER, R ;

SPREITZ, J ;

FABER, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1365-1368

[4] CHEMOENZYMATIC SYNTHESIS OF CARBOCYCLIC OXETANOCIN-A INVOLVING A NOVEL PHOTOCHEMICAL-REARRANGEMENT [J].

COTTERILL, IC ;

ROBERTS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (20) :2585-2586

[5] ENANTIO-COMPLEMENTARY TOTAL ASYMMETRIC SYNTHESES OF PROSTAGLANDIN-E2 AND PROSTAGLANDIN-F2-ALPHA [J].

DAVIES, J ;

ROBERTS, SM ;

REYNOLDS, DP ;

NEWTON, RF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1317-1320

[6] Unusual amino acids .7. Asymmetric synthesis of 3- and 4-pyridylalanines [J].

Dobler, C ;

Kreuzfeld, HJ ;

Michalik, M ;

Krause, HW .

TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :117-125

[7] Microbial reduction of methyl-substituted bicyclo[3.2.0]hept-3-en-6-ones: A screening to homochiral endo- and exo-alcohols [J].

Fantin, G ;

Fogagnolo, M ;

Medici, A ;

Pedrini, P ;

Marotta, E ;

Monti, M ;

Righi, P .

TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :277-282

[8] ELECTROPHILIC BROMINATION OF BICYCLO[3,3,0]HEPT-2-EN-6-ONES [J].

GRUDZINSKI, Z ;

ROBERTS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (18) :1767-1773

[9] Enantioselective hydrogenation of dehydroamino acid derivatives using PINDOPHOS-rhodium as chiral catalyst [J].

Kreuzfeld, HJ ;

Schmidt, U ;

Dobler, C ;

Krause, HW .

TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1011-1018

[10] SUBSTRATE NON-ENANTIOSPECIFIC AND PRODUCT ENANTIOSELECTIVE REDUCTION OF BICYCLO[3.2.0]HEPT-2-EN-6-ONE USING YEAST [J].

NEWTON, RF ;

PATON, J ;

REYNOLDS, DP ;

YOUNG, S ;

ROBERTS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (20) :908-909

← 1 2 →