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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 52期

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

页码：9773 / 9776

页数：4

共 26 条

[1] Total synthesis of (+)-isolaurepinnacin. Use of acetal-alkene cyclization to prepare highly functionalized seven-membered cyclic ethers
Berger, D
Overman, LE
Renhowe, PA
[J]. 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
BRADLEY, DH
KHAN, MA
NICHOLAS, KM
[J]. 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
CAFFYN, AJM
NICHOLAS, KM
[J]. 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
CARLSEN, PHJ
KATSUKI, T
MARTIN, VS
SHARPLESS, KB
[J]. 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
JACOBI, PA
RAJESWARI, S
[J]. 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
JACOBI, PA
ZHENG, WJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (16) : 2581 - 2584
[9] AN UNEQUIVOCAL SYNTHESIS OF THE RING-A,B DIHYDROPYRROMETHENONE OF PHYTOCHROME
JACOBI, PA
GUO, JS
ZHENG, WJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (08) : 1197 - 1200
[10] Addition of hexacarbonyldicobalt-stabilized propargyl cations to alkenes
Krafft, ME
Cheung, YY
Wright, C
Cali, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3912 - 3915

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