Novel catalytic kinetic resolution of racemic epoxides to allylic alcohols

被引:38
作者
Gayet, A [1 ]
Bertilsson, S [1 ]
Andersson, PG [1 ]
机构
[1] Uppsala Univ, Inst Chem, Dept Organ Chem, S-75121 Uppsala, Sweden
关键词
D O I
10.1021/ol025983e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic The kinetic resolution of racemic epoxides via catalytic enantioselective rearrangement to allylic alcohols was investigated. Using the U-salt of (1S,3R,4R)-3-(pyrrolidinyl)methyl-2-azabicyclo [2.2.1] heptane 1 as catalyst allowed both epoxides and allylic alcohols to be obtained in an enantioenriched form.
引用
收藏
页码:3777 / 3779
页数:3
相关论文
共 21 条
[11]   Enantioselective desymmetrisation of achiral epoxides [J].
Hodgson, DM ;
Gibbs, AR ;
Lee, GP .
TETRAHEDRON, 1996, 52 (46) :14361-14384
[12]  
Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4
[13]   Various aspects of the reaction of a chiral catalyst or reagent with a racemic or enantiopure substrate [J].
Kagan, HB .
TETRAHEDRON, 2001, 57 (13) :2449-2459
[14]  
Keith JM, 2001, ADV SYNTH CATAL, V343, P5, DOI 10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO
[15]  
2-I
[16]   DILITHIATED AMINOALCOHOLS AS HOMOCHIRAL BASES [J].
MILNE, D ;
MURPHY, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (10) :884-886
[17]   PHEROMONE SYNTHESIS .101. SYNTHESIS AND BIOACTIVITY OF OPTICALLY-ACTIVE FORMS OF 1-METHYL-2-CYCLOHEXEN-1-OL, AN AGGREGATION PHEROMONE DENDROCTONUS-PSEUDOTSUGAE [J].
MORI, K ;
HAZRA, BG ;
PFEIFFER, RJ ;
GUPTA, AK ;
LINDGREN, BS .
TETRAHEDRON, 1987, 43 (10) :2249-2254
[18]   Recent advances in asymmetric synthesis using chiral lithium amide bases [J].
O'Brien, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (08) :1439-1457
[19]   New and highly enantioselective catalysts for the rearrangement of meso-epoxides into chiral allylic alcohols [J].
Södergren, MJ ;
Andersson, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10760-10761
[20]   Allylic alcohols via catalytic asymmetric epoxide rearrangement [J].
Södergren, MJ ;
Bertilsson, SK ;
Andersson, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) :6610-6618