Stereoselective dioxygenase-catalysed benzylic hydroxylation at prochiral methylene groups in the chemoenzymatic synthesis of enantiopure vicinal aminoindanols.

被引:43
作者
Boyd, DR
Sharma, ND
Bowers, NI
Goodrich, PA
Groocock, MR
Blacker, AJ
Clarke, DA
Howard, T
Dalton, H
机构
[1] ZENECA PTD,HUDDERSFIELD HD2 1FF,YORKS,ENGLAND
[2] UNIV WARWICK,DEPT BIOL SCI,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND
关键词
D O I
10.1016/0957-4166(96)00180-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiopure benzylic alcohols containing two stereogenic centres in a cis-relationship result from stereoselective monohydroxylation of achiral 2-substituted indans in cultures of Pseudomonas putida UV4 and are used in the chemoenzymatic synthesis of both cis- and trans-aminoindanol enantiomers. (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1559 / 1562
页数:4
相关论文
共 22 条
[1]   ENANTIOSELECTIVE BACTERIAL BIOTRANSFORMATION ROUTES TO CIS-DIOL METABOLITES OF MONOSUBSTITUTED BENZENES, NAPHTHALENE AND BENZOCYCLOALKENES OF EITHER ABSOLUTE-CONFIGURATION [J].
ALLEN, CCR ;
BOYD, DR ;
DALTON, H ;
SHARMA, ND ;
BRANNIGAN, I ;
KERLEY, NA ;
SHELDRAKE, GN ;
TAYLOR, SC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :117-118
[2]  
ALLEN CCR, 1995, J CHEM SOC CHEM COMM, P119
[3]   STEREOSPECIFIC BENZYLIC HYDROXYLATION OF BICYCLIC ALKENES BY PSEUDOMONAS-PUTIDA - ISOLATION OF (+)-R-1-HYDROXY-1,2-DIHYDRONAPHTHALENE, AN ARENE HYDRATE OF NAPHTHALENE FROM METABOLISM OF 1,2-DIHYDRONAPHTHALENE [J].
BOYD, DR ;
MCMORDIE, RAS ;
SHARMA, ND ;
DALTON, H ;
WILLIAMS, P ;
JENKINS, RO .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (06) :339-340
[4]  
BOYD DR, 1991, TETRAHEDRON LETT, V32, P3887
[5]   CHEMICAL SYNTHESIS AND OPTICAL PURITY DETERMINATION OF OPTICALLY-ACTIVE 1,2-EPOXYINDAN AND ALCOHOL PRODUCTS WHICH ARE ALSO DERIVED FROM MAMMALIAN OR MICROBIAL-METABOLISM OF INDENE OR INDANONES [J].
BOYD, DR ;
SHARMA, ND ;
SMITH, AE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (11) :2767-2770
[6]  
BOYD DR, 1995, ORGANIC REACTIVITY P, P130
[7]  
BOYD DR, 1996, J CHEM SOC P1, P64
[8]   MECHANISTIC STUDIES ON DNA PHOTOLYASE .3. THE TRAPPING OF THE ONE-BOND-CLEAVED INTERMEDIATE FROM A PHOTODIMER RADICAL CATION MODEL SYSTEM [J].
BURDI, D ;
BEGLEY, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7768-7770
[9]   HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION MEDIATED BY A CHIRAL AUXILIARY DERIVED FROM AMINO INDANOL - THE ROLE OF CONFORMATION ON DIASTEREOSELECTIVITY [J].
DAVIES, IW ;
SENANAYAKE, CH ;
CASTONGUAY, L ;
LARSEN, RD ;
VERHOEVEN, TR ;
REIDER, PJ .
TETRAHEDRON LETTERS, 1995, 36 (42) :7619-7622
[10]   CHEMOENZYMATIC SYNTHESIS OF 1,2-AMINO-ALCOHOLS AND 1,3-AMINO-ALCOHOLS AND THEIR USE IN THE ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE AND ANTI-ACETOPHENONE OXIME METHYL-ETHER WITH BORANE [J].
DIDIER, E ;
LOUBINOUX, B ;
TOMBO, GMR ;
RIHS, G .
TETRAHEDRON, 1991, 47 (27) :4941-4958