NEW ENTRY TO C2 SYMMETRICAL TRANS-2,6-BIS(HYDROXYMETHYL)PIPERIDINE-DERIVATIVES VIA THE SHARPLESS ASYMMETRIC DIHYDROXYLATION

被引:20
作者
TAKAHATA, H
KOUNO, S
MOMOSE, T
机构
[1] Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Toyama, 930-01
关键词
D O I
10.1016/0957-4166(95)00131-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new synthesis of both enantiomers of C-2-symmetric trans-2,6-bis(hydroxymethyl)piperidine derivatives 1 by the use, as a key reaction, of the Sharpless asymmetric dihydroxylation of a symmetric diene 2 is presented.
引用
收藏
页码:1085 / 1088
页数:4
相关论文
共 16 条
[1]   IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].
CRISPINO, GA ;
JEONG, KS ;
KOLB, HC ;
WANG, ZM ;
XU, DQ ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786
[2]   ASYMMETRIC REACTIONS USING C-2-SYMMETRICALLY 2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES [J].
KATSUKI, T ;
YAMAGUCHI, M .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1986, 44 (06) :532-544
[3]   ASYMMETRIC ALKYLATION OF CARBOXYAMIDES BY USING TRANS-2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES [J].
KAWANAMI, Y ;
ITO, Y ;
KITAGAWA, T ;
TANIGUCHI, Y ;
KATSUKI, T ;
YAMAGUCHI, M .
TETRAHEDRON LETTERS, 1984, 25 (08) :857-860
[4]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[5]   SYNTHESIS OF ENANTIOMERICALLY PURE (2R,5R) DISUBSTITUTED PYRROLIDINES FROM D-MANNITOL [J].
MARZI, M ;
MINETTI, P ;
MISITI, D .
TETRAHEDRON, 1992, 48 (46) :10127-10132
[6]   DOUBLY DIASTEREOSELECTIVE IODOLACTONIZATIONS - OLEFIN AND FACE SELECTIVITY IN NONA-2,7-DIENE-5-CARBOXYLIC ACID CYCLIZATIONS [J].
MCKEW, JC ;
OLMSTEAD, MM ;
KURTH, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3389-3393
[7]   PREPARATION OF NONRACEMIC 3,5-DISUBSTITUTED-GAMMA-BUTYROLACTONES - AN EFFECTIVE SEQUENT AUXILIARY FOR AMIDE ALKYLATION AND IODOLACTONIZATION [J].
MOON, HS ;
EISENBERG, SWE ;
WILSON, ME ;
SCHORE, NE ;
KURTH, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6504-6505
[8]   SYNTHESIS OF (2R,6R)-(-)-2,6-LUPETIDINE - 2,6-DISUBSTITUTED PIPERIDINES AS POTENTIALLY USEFUL C2-SYMMETRIC CHIRAL REAGENTS [J].
NAJDI, S ;
KURTH, MJ .
TETRAHEDRON LETTERS, 1990, 31 (23) :3279-3282
[9]   ENANTIOSELECTIVE ROUTE TO GAMMA-BUTYROLACTONES - CHIRAL AUXILIARY MEDIATED AMIDE ALKYLATION AND IODOLACTONIZATION [J].
NAJDI, S ;
REICHLIN, D ;
KURTH, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6241-6244
[10]   THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT [J].
SHARPLESS, KB ;
AMBERG, W ;
BENNANI, YL ;
CRISPINO, GA ;
HARTUNG, J ;
JEONG, KS ;
KWONG, HL ;
MORIKAWA, K ;
WANG, ZM ;
XU, DQ ;
ZHANG, XL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2768-2771