Use of asymmetric propargyl dicobalt hexacarbonyl complexes in organic synthesis:: Access to enantiomerically pure α-hydroxy acid derivatives

被引:18
作者
Betancort, JM [1 ]
Rodríguez, CM [1 ]
Martín, VS [1 ]
机构
[1] Univ La Laguna, CSIC, Inst Univ Bioorgan Antonio Gonzalez, E-38206 La Laguna, Tenerife, Spain
关键词
Nicholas reaction; asymmetric synthesis;
D O I
10.1016/S0040-4039(98)02170-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The trapping under different conditions of the carbocation generated by acid treatment of chiral Co-2(CO)(6)-complexed propargylic secondary alcohols permitted access to either diastereoisomer at the propargylic center. Further chemical manipulations provided either enantiomer of enantiomerically pure 1,2-difunctionalized molecules such as 1,2-diols, alpha-hydroxy-aldehydes or alpha-hydroxy-acids. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9773 / 9776
页数:4
相关论文
共 26 条
[1]   Total synthesis of (+)-isolaurepinnacin. Use of acetal-alkene cyclization to prepare highly functionalized seven-membered cyclic ethers [J].
Berger, D ;
Overman, LE ;
Renhowe, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) :2446-2452
[2]   PREPARATION, SOLUTION STRUCTURES, AND NUCLEOPHILIC REACTIONS OF CHIRAL, BIMETALLIC COMPLEXES - [(MU-ETA-2,ETA-3-PROPARGYLIUM)CO2(CO)5P(C6H5)3]BF4 [J].
BRADLEY, DH ;
KHAN, MA ;
NICHOLAS, KM .
ORGANOMETALLICS, 1992, 11 (07) :2598-2607
[3]   STEREOSELECTIVE PROPARGYLATION MEDIATED BY A CHIRAL METAL CLUSTER - REACTIONS OF [(PROPARGYLIUM)CO2(CO)5-(P(OR)3)][BF4] WITH CARBON NUCLEOPHILES [J].
CAFFYN, AJM ;
NICHOLAS, KM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6438-6439
[4]  
CAFFYN AJM, 1995, COMPREHENSIVE ORGANO, V12, P685
[5]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[6]  
ISOBE M, 1994, SYNLETT, P916
[7]   TETRAPYRROLES .3. HOMOCHIRAL DIHYDROPYRROMETHENONES FROM N-AMINOPYRROLES AND ACETYLENIC ACIDS [J].
JACOBI, PA ;
RAJESWARI, S .
TETRAHEDRON LETTERS, 1992, 33 (42) :6231-6234
[8]   A VERSATILE SYNTHESIS OF BETA-AMINO ACIDS USING THE NICHOLAS REACTION .1. APPLICATION TO BETA-LACTAMS OF THE CARBAPENEM CLASS [J].
JACOBI, PA ;
ZHENG, WJ .
TETRAHEDRON LETTERS, 1993, 34 (16) :2581-2584
[9]   AN UNEQUIVOCAL SYNTHESIS OF THE RING-A,B DIHYDROPYRROMETHENONE OF PHYTOCHROME [J].
JACOBI, PA ;
GUO, JS ;
ZHENG, WJ .
TETRAHEDRON LETTERS, 1995, 36 (08) :1197-1200
[10]   Addition of hexacarbonyldicobalt-stabilized propargyl cations to alkenes [J].
Krafft, ME ;
Cheung, YY ;
Wright, C ;
Cali, R .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3912-3915