NEW ENANTIOSELECTIVE SYNTHESES OF ACETYLENIC ALCOHOLS USING FUNCTIONALIZED DIORGANOZINCS

被引：38

作者：

LUTJENS, H ^{[1
]}

NOWOTNY, S ^{[1
]}

KNOCHEL, P ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 11期

关键词：

D O I：

10.1016/0957-4166(95)00355-S

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two new enantioselective preparations of polyfunctional propargylic alcohols (82 to >96 % ee) have been developed. They were obtained by using the addition of functionalized dialkylzincs to acetylenic aldehydes in the presence of a 1:1 mixture of Ti(Oi-Pr)(4) and Ti(Ot-Bu)(4) and I as a catalyst. In a second method, dialkylzincs were added to alpha-bromo-alpha,beta-unsaturated aldehydes leading to allylic bromo-alcohols (84 to > 96 % ee) which were smoothly converted to propargylic alcohols by treatment with NaH in DMF (25 degrees C, 10 min).

引用

页码：2675 / 2678

页数：4

共 34 条

[1] MECHANISTIC ASPECTS ON THE FORMATION OF CHIRAL ALLENES FROM PROPARGYLIC ETHERS AND ORGANOCOPPER REAGENTS
ALEXAKIS, A
MAREK, I
MANGENEY, P
NORMANT, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) : 8042 - 8047
[2] Brieden W., 1993, ANGEW CHEM, V105, P629
[3] 4-HYDROXYNON-2-ENAL, A CYTOTOXIC LIPID-PEROXIDATION PRODUCT, AND ITS C-5-ANALOG 4-HYDROXYPENT-2-ENAL - ENANTIOSELECTIVE SYNTHESIS AND STEREOANALYSIS
BRINGMANN, G
GASSEN, M
LARDY, R
[J]. TETRAHEDRON, 1994, 50 (34) : 10245 - 10252
[4] ASYMMETRIC REDUCTION - REDUCTION OF ACETYLENIC KETONES WITH CHIRAL HYDRIDE AGENT
BRINKMEYER, RS
KAPOOR, VM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) : 8339 - 8341
[5] ASYMMETRIC REDUCTIONS OF ALPHA,BETA-ACETYLENIC KETONES AND ACETOPHENONE USING LITHIUM ALUMINUM-HYDRIDE COMPLEXED WITH OPTICALLY-ACTIVE 1,3-AMINO ALCOHOLS
COHEN, N
LOPRESTI, RJ
NEUKOM, C
SAUCY, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (04) : 582 - 588
[6] CATALYTIC ASYMMETRIC PREPARATION OF POLYFUNCTIONAL PROTECTED 1,2-DIOLS AND EPOXIDES
EISENBERG, C
KNOCHEL, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) : 3760 - 3761
[7] ON THE LITHIUM DIMETHYLCUPRATE INDUCED CONVERSION OF PROPARGYLIC ESTERS INTO ALLENES USING A STEROIDAL C/D FRAGMENT DERIVED FROM VITAMIN-D3 AS A STEREOCHEMICAL PROBE
HACES, A
VANKRUCHTEN, EMGA
OKAMURA, WH
[J]. TETRAHEDRON LETTERS, 1982, 23 (27) : 2707 - 2710
[8] PRACTICAL METHOD FOR SYNTHESIS OF OPTICALLY PURE PROPARGYLIC ALCOHOLS
ITO, T
OKAMOTO, S
SATO, F
[J]. TETRAHEDRON LETTERS, 1989, 30 (50) : 7083 - 7086
[9] A NEW CATALYTIC ASYMMETRIC APPROACH TO POLYFUNCTIONAL ALDOL PRODUCTS MEDIATED BY ZINC ORGANOMETALLICS
KNOCHEL, P
BRIEDEN, W
ROZEMA, MJ
EISENBERG, C
[J]. TETRAHEDRON LETTERS, 1993, 34 (37) : 5881 - 5884
[10] ALPHA-KETO DIANION PRECURSORS VIA CONJUGATE ADDITIONS TO CYCLIC ALPHA-BROMO ENONES
KOWALSKI, CJ
WEBER, AE
FIELDS, KW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) : 5088 - 5093

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