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

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 05期

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

页码：1085 / 1088

页数：4

共 16 条

[1] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS
CRISPINO, GA
JEONG, KS
KOLB, HC
WANG, ZM
XU, DQ
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 3785 - 3786
[2] ASYMMETRIC REACTIONS USING C-2-SYMMETRICALLY 2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES
KATSUKI, T
YAMAGUCHI, M
[J]. 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
KAWANAMI, Y
ITO, Y
KITAGAWA, T
TANIGUCHI, Y
KATSUKI, T
YAMAGUCHI, M
[J]. TETRAHEDRON LETTERS, 1984, 25 (08) : 857 - 860
[4] CATALYTIC ASYMMETRIC DIHYDROXYLATION
KOLB, HC
VANNIEUWENHZE, MS
SHARPLESS, KB
[J]. CHEMICAL REVIEWS, 1994, 94 (08) : 2483 - 2547
[5] SYNTHESIS OF ENANTIOMERICALLY PURE (2R,5R) DISUBSTITUTED PYRROLIDINES FROM D-MANNITOL
MARZI, M
MINETTI, P
MISITI, D
[J]. TETRAHEDRON, 1992, 48 (46) : 10127 - 10132
[6] DOUBLY DIASTEREOSELECTIVE IODOLACTONIZATIONS - OLEFIN AND FACE SELECTIVITY IN NONA-2,7-DIENE-5-CARBOXYLIC ACID CYCLIZATIONS
MCKEW, JC
OLMSTEAD, MM
KURTH, MJ
[J]. 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
MOON, HS
EISENBERG, SWE
WILSON, ME
SCHORE, NE
KURTH, MJ
[J]. 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
NAJDI, S
KURTH, MJ
[J]. TETRAHEDRON LETTERS, 1990, 31 (23) : 3279 - 3282
[9] ENANTIOSELECTIVE ROUTE TO GAMMA-BUTYROLACTONES - CHIRAL AUXILIARY MEDIATED AMIDE ALKYLATION AND IODOLACTONIZATION
NAJDI, S
REICHLIN, D
KURTH, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) : 6241 - 6244
[10] THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT
SHARPLESS, KB
AMBERG, W
BENNANI, YL
CRISPINO, GA
HARTUNG, J
JEONG, KS
KWONG, HL
MORIKAWA, K
WANG, ZM
XU, DQ
ZHANG, XL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) : 2768 - 2771

← 1 2 →