PROTECTING GROUP CONTROLLED DIASTEREOSELECTIVE REDUCTION OF DIPROTECTED ALPHA,ALPHA-BIS(HYDROXYMETHYL)KETONES DERIVED FROM THYM-ASTERISK, USING THE DIBALH MGBR2 SYSTEM

被引：26

作者：

GUANTI, G ^{[1
]}

BANFI, L ^{[1
]}

RIVA, R ^{[1
]}

ZANNETTI, MT ^{[1
]}

机构：

[1] CNR,CTR STUDIO CHIM COMPOSTI CICLOALIFAT & AROMAT,I-16132 GENOA,ITALY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(00)73940-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of diprotected alpha,alpha-bis(hydroxymethyl)ketones 5, derived from the novel chiral building blocks THYM* 1 and BHYMA* 2 has been realized with good to excellent stereoselectivity (from 85:15 to 97:3), through a appropriate choice of the two protecting groups and by employing the combination of DIBALH and MgBr2.Et2O.

引用

页码：5483 / 5486

页数：4

共 16 条

[1] BANFI L, UNPUB TETRAHEDRON LE
[2] BONINI C, 1991, GAZZ CHIM ITAL, V121, P75
[3] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES
CHEN, KM
HARDTMANN, GE
PRASAD, K
REPIC, O
SHAPIRO, MJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 155 - 158
[4] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
EVANS, DA
CHAPMAN, KT
CARREIRA, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) : 3560 - 3578
[5] REDUCTION OF BETA-HYDROXY KETONES WITH CATECHOLBORANE - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF SYN 1,3-DIOLS
EVANS, DA
HOVEYDA, AH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) : 5190 - 5192
[6] ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE AS A HIGHLY STEREODIVERGENT CHIRAL BUILDING BLOCK - PREPARATION OF ALL 4 STEREOISOMERS OF PROTECTED 2-HYDROXYMETHYL-1,3-BUTANEDIOL
GUANTI, G
BANFI, L
NARISANO, E
[J]. TETRAHEDRON LETTERS, 1990, 31 (44) : 6421 - 6424
[7] ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF C11-C17 FRAGMENT OF TYLONOLIDE FROM ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE
GUANTI, G
BANFI, L
GHIRON, C
NARISANO, E
[J]. TETRAHEDRON LETTERS, 1991, 32 (02) : 267 - 270
[8] SYNTHESIS OF BOTH TOP AND BOTTOM FRAGMENTS OF (-)-TALAROMYCIN-A THROUGH ENANTIOSPECIFIC AND DIASTEREOSELECTIVE ELABORATION OF ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE
GUANTI, G
BANFI, L
NARISANO, E
ZANNETTI, MT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) : 1508 - 1514
[9] PROTECTING GROUP CONTROLLED DIASTEREOSELECTIVE ALLYLATION OF ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDES (BHYMA-STAR)
GUANTI, G
BANFI, L
NARISANO, E
[J]. TETRAHEDRON LETTERS, 1991, 32 (47) : 6939 - 6942
[10] CHEMOENZYMATIC PREPARATION OF ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE (THYM-STAR) AND OF ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDE (BHYMA-STAR) AS NEW HIGHLY VERSATILE CHIRAL BUILDING-BLOCKS
GUANTI, G
BANFI, L
NARISANO, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1540 - 1554

← 1 2 →