AXIALLY CHIRAL ALLENYLBORANES - CATALYTIC ASYMMETRIC-SYNTHESIS BY PALLADIUM-CATALYZED HYDROBORATION OF BUT-1-EN-3-YNES AND THEIR REACTION WITH AN ALDEHYDE

被引：109

作者：

MATSUMOTO, Y

NAITO, M

UOZUMI, Y

HAYASHI, T

机构：

[1] HOKKAIDO UNIV,CTR CATALYSIS RES,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN

[2] HOKKAIDO UNIV,GRAD SCH PHARMACEUT SCI,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 19期

关键词：

D O I：

10.1039/c39930001468

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of but-1-en-3-ynes(CH2=CR-C=CH: R=H, n-C5H11) with catecholborane in the presence of a palladium catalyst bearing a chiral monodentate phosphine ligand, (S)-(-)-MeO-MOP, give optically active (3-substituted-1,2-butadienyl)-1,3,2-benzodioxaborolanes [Me(R)C=C=CH(BO2C6H4)], the reaction of which with benzaldehyde proceeded with syn attack to give the corresponding optically active but-3-ynyl alcohols of up to 61% enantiomeric excess (e.e.).

引用

页码：1468 / 1469

页数：2

共 50 条

[21] CATALYTIC ASYMMETRIC-SYNTHESIS OF QUATERNARY CARBON CENTERS - PALLADIUM-CATALYZED FORMATION OF EITHER ENANTIOMER OF SPIROOXINDOLES AND RELATED SPIROCYCLICS
ASHIMORI, A
OVERMAN, LE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 405 - ORGN
[22] Palladium-catalyzed asymmetric synthesis of axially chiral (Allenylmethyl)silanes and chirality transfer to stereogenic carbon centers in SE′ reactions
Ogasawara, M
Ueyama, K
Nagano, T
Mizuhata, Y
Hayashi, T
ORGANIC LETTERS, 2003, 5 (02) : 217 - 219
[23] PALLADIUM-CATALYZED ASYMMETRIC 1,4-DISILYLATION OF ALPHA,BETA-UNSATURATED KETONES - CATALYTIC ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY KETONES
HAYASHI, T
MATSUMOTO, Y
ITO, Y
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (16) : 5579 - 5581
[24] CATALYTIC ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY KETONES BY PALLADIUM-CATALYZED ASYMMETRIC 1,4-DISILYLATION OF ALPHA,BETA-UNSATURATED KETONES
MATSUMOTO, Y
HAYASHI, T
ITO, Y
TETRAHEDRON, 1994, 50 (02) : 335 - 346
[25] ASYMMETRIC-SYNTHESIS VIA AXIALLY DISSYMMETRIC MOLECULES .3. ASYMMETRIC-SYNTHESIS OF CHIRAL GERANIOL-1-D AND RELATED TERPENIC ALCOHOLS
NISHIZAWA, M
NOYORI, R
TETRAHEDRON LETTERS, 1980, 21 (29) : 2821 - 2824
[26] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .2. NICKEL-CATALYZED AND PALLADIUM-CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING
HAYASHI, T
KONISHI, M
FUKUSHIMA, M
MISE, T
KAGOTANI, M
TAJIKA, M
KUMADA, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) : 180 - 186
[27] Palladium-catalyzed asymmetric synthesis of N,N-dibenzylcyclohex-2-en-1-amine
Gavrilov, K. N.
Zheglov, S. V.
Gavrilov, V. K.
Maksimova, M. G.
Zamilatskov, I. A.
RUSSIAN CHEMICAL BULLETIN, 2015, 64 (04) : 967 - 969
[28] Palladium-catalyzed asymmetric synthesis of N,N-dibenzylcyclohex-2-en-1-amine
K. N. Gavrilov
S. V. Zheglov
V. K. Gavrilov
M. G. Maksimova
I. A. Zamilatskov
Russian Chemical Bulletin, 2015, 64 : 967 - 969
[29] Palladium-Catalyzed Asymmetric 1,6-Addition of Diarylphosphines to Allylidenemalonates for Chiral Phosphine Synthesis
Wei, Xu
Lu, Junzhu
Duan, Wei-Liang
SYNTHESIS-STUTTGART, 2016, 48 (23): : 4155 - 4160
[30] CATALYTIC ASYMMETRIC-SYNTHESIS OF QUARTERNARY CARBON CENTERS - PALLADIUM-CATALYZED FORMATION OF EITHER ENANTIOMER OF SPIROOXINDOLES AND RELATED SPIROCYCLICS USING A SINGLE ENANTIOMER OF A CHIRAL DIPHOSPHINE LIGAND
ASHIMORI, A
OVERMAN, LE
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17): : 4571 - 4572

← 1 2 3 4 5 →