VINYL CARBONATES AS NOVEL ALKOXYCARBONYLATION REAGENTS IN ENZYMATIC-SYNTHESIS OF CARBONATES

被引:50
作者
POZO, M [1 ]
PULIDO, R [1 ]
GOTOR, V [1 ]
机构
[1] UNIV OVIEDO,FAC QUIM,DEPT QUIM ORGAN & INORGAN,E-33071 OVIEDO,SPAIN
关键词
VINYL CARBONATES; ENZYMATIC ALKOXYCARBONYLATION; CARBAMATES; CHIRAL CARBONATES; ENANTIOSELECTIVITY;
D O I
10.1016/S0040-4020(01)88237-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carbonates could be obtained by enzymatic alkoxycarbonylation from vinyl carbonates, which are easily prepared from vinyl chloroformate. The reaction was catalyzed by Candida antarctica lipases, SP 435 and SP 435 A. The method could be also used for the synthesis of carbamates. When racemic alcohols were used, lipase catalyzed their resolution, and chiral carbonates were obtained with different enantiomeric excesses depending upon the structure of the alcohol.
引用
收藏
页码:6477 / 6484
页数:8
相关论文
共 12 条
[1]   ENZYMATIC TRANSESTERIFICATIONS OF CARBONATES IN WATER-RESTRICTED ENVIRONMENTS [J].
ABRAMOWICZ, DA ;
KEESE, CR .
BIOTECHNOLOGY AND BIOENGINEERING, 1989, 33 (02) :149-156
[2]   ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS [J].
BIANCHI, D ;
CESTI, P ;
BATTISTEL, E .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5531-5534
[3]  
BOLAND W, 1991, SYNTHESIS-STUTTGART, P1049
[4]  
DAVIES HG, 1989, BIOTRANSFORMATIONS P
[5]   ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS [J].
DEGUEILCASTAING, M ;
DEJESO, B ;
DROUILLARD, S ;
MAILLARD, B .
TETRAHEDRON LETTERS, 1987, 28 (09) :953-954
[6]   NOVEL ROUTE TO CHIRAL POLYMERS INVOLVING BIOCATALYTIC TRANSESTERIFICATION OF O-ACRYLOYL OXIMES [J].
GHOGARE, A ;
KUMAR, GS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (02) :134-135
[7]   OXIME ESTERS AS NOVEL IRREVERSIBLE ACYL TRANSFER AGENTS FOR LIPASE CATALYSIS IN ORGANIC MEDIA [J].
GHOGARE, A ;
KUMAR, GS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (20) :1533-1535
[8]   RESOLUTION OF RACEMIC MIXTURES VIA LIPASE CATALYSIS IN ORGANIC-SOLVENTS [J].
KIRCHNER, G ;
SCOLLAR, MP ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7072-7076
[9]   EVOLUTION OF A SERIES OF PEPTIDOLEUKOTRIENE ANTAGONISTS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF 1,3,5-SUBSTITUTED INDOLES AND INDAZOLES [J].
MATASSA, VG ;
MADUSKUIE, TP ;
SHAPIRO, HS ;
HESP, B ;
SNYDER, DW ;
AHARONY, D ;
KRELL, RD ;
KEITH, RA .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1781-1790
[10]   A NOVEL AND CONVENIENT ROUTE TO 3'-CARBONATES FROM UNPROTECTED 2'-DEOXYNUCLEOSIDES THROUGH AN ENZYMATIC-REACTION [J].
MORIS, F ;
GOTOR, V .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2490-2492