TITANIUM AND BORON MEDIATED ALDOL REACTIONS OF BETA-HYDROXY KETONES

被引：45
作者：
LUKE, GP
MORRIS, J
机构：
[1] Medicinal Chemistry Research, The Upjohn Company, Kalamazoo
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 10期
关键词：
D O I：
10.1021/jo00115a015
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of enolates derived from titanium and boron complexes of beta-hydroxy ketones with aldehydes afforded aldol products in good to excellent yields. Whereas the boron mediated reactions gave exclusively anti aldol products derived from the reaction at C-alpha, the titanium mediated reactions produced primarily syn aldol products from reaction at C-alpha. The product selectivities observed in the titanium mediated aldol reactions were highly dependent on the substitution pattern of the starting beta-hydroxy ketone.
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页码：3013 / 3019
页数：7
相关论文
共 44 条
[1]   ASYMMETRIC ALDOL REACTIONS EMPLOYING A CAMPHOR-DERIVED CHIRAL OXAZINONE AUXILIARY [J].
AHN, KH ;
LEE, SK ;
LIM, AK .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5065-5066
[2]   DIASTEREOSELECTIVE SYNTHESIS OF ANTI AND SYN ALPHA,BETA-DIHYDROXY THIOESTERS BY TITANIUM ENOLATE ALDOL CONDENSATION [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
BORGIA, AL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6339-6342
[3]   ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES [J].
BONNER, MP ;
THORNTON, ER .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1299-1308
[4]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].
CHEN, KM ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
TETRAHEDRON LETTERS, 1987, 28 (02) :155-158
[5]  
CHOUDHURY A, 1992, TETRAHEDRON, V48, P5701
[6]   DIASTEREOSELECTIVE ALDOL ADDITION USING BORON-TRICHLORIDE OR ALKOXYDICHLOROBORANE [J].
CHOW, HF ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1986, 69 (03) :604-614
[7]   STEREOSELECTIVE ALDOL REACTION WITH CHIRAL SECONDARY ACETAMIDES [J].
DEVANT, R ;
BRAUN, M .
CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (07) :2191-2207
[8]   DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALDOL REACTIONS VIA ALPHA-SILYL KETONES, ASYMMETRIC-SYNTHESIS OF THE AGGREGATION PHEROMONE SITOPHILURE [J].
ENDERS, D ;
LOHRAY, BB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (04) :581-583
[9]   DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].
EVANS, DA ;
CHAPMAN, KT ;
CARREIRA, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578
[10]   NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].
EVANS, DA ;
URPI, F ;
SOMERS, TC ;
CLARK, JS ;
BILODEAU, MT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216
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