Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations

被引：13

作者：

Medina, Casey ^{[1
]}

Carter, Kyle P. ^{[1
]}

Miller, Michael ^{[1
]}

Clark, Timothy B. ^{[2
]}

O'Neil, Gregory W. ^{[1
]}

机构：

[1] Western Washington Univ, Dept Chem, Bellingham, WA 98225 USA

[2] Univ San Diego, Dept Chem, San Diego, CA 92110 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 18期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

SI-H BOND; ALPHA; BETA-UNSATURATED COMPOUNDS; BETA-BORATION; AMINE BASE; REACTIVITY; SILICON; KETONES; (+)-DISCODERMOLIDE; CONVERSION; INDUCTION;

D O I：

10.1021/jo401293a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.

引用

页码：9093 / 9101

页数：9

共 47 条

[1] REACTIONS OF TRIETHYLSILANE AND DIETHYLSILANE WITH INORGANIC HALIDES AND ACIDS [J].

ANDERSON, HH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (19) :5083-5085

[2] INTRAMOLECULAR HYDROSILYLATIONS .2. THE ANTI-SELECTIVE REDUCTION OF BETA-HYDROXYKETONES [J].

ANWAR, S ;

DAVIS, AP .

TETRAHEDRON, 1988, 44 (13) :3761-3770

[3]

Anwar S., 1986, J CHEM SOC CHEM COMM, V831

[4] HYDROGEN-BONDING TO COORDINATED IMIDAZOLE - ASSOCIATION OF 1,10-PHENANTHROLINE AND OTHER BASES WITH BIS(IMIDAZOLE)METALLOPORPHYRINS [J].

BALCH, AL ;

WATKINS, JJ ;

DOONAN, DJ .

INORGANIC CHEMISTRY, 1979, 18 (05) :1228-1231

[5] Metal-Free Catalytic Boration at the β-Position of α,β-Unsaturated Compounds: A Challenging Asymmetric Induction [J].

Bonet, Amadeu ;

Gulyas, Henrik ;

Fernandez, Elena .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (30) :5130-5134

[6] HYDROGENOSILANES - PENTACOORDINATION AND PSEUDOROTATION [J].

BOYER, J ;

CORRIU, RJP ;

KPOTON, A ;

MAZHAR, M ;

POIRIER, M ;

ROYO, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 301 (02) :131-135

[7] ENHANCEMENT OF SI-H BOND REACTIVITY IN PENTACOORDINATED STRUCTURES [J].

BOYER, J ;

BRELIERE, C ;

CORRIU, RJP ;

KPOTON, A ;

POIRIER, M ;

ROYO, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 311 (03) :C39-C43

[8] PENTACOORDINATED SILICON HYDRIDES - VERY HIGH-AFFINITY OF THE SI-H BOND FOR THE EQUATORIAL POSITION [J].

BRELIERE, C ;

CARRE, F ;

CORRIU, RJP ;

POIRIER, M ;

ROYO, G .

ORGANOMETALLICS, 1986, 5 (02) :388-390

[9] Catalytic Enantioselective Conjugate Allylation of Unsaturated Methylidene Ketones [J].

Brozek, Laura A. ;

Sieber, Joshua D. ;

Morken, James P. .

ORGANIC LETTERS, 2011, 13 (05) :995-997

[10] Catalytic methodologies for the β-boration of conjugated electron deficient alkenes [J].

Calow, Adam D. J. ;

Whiting, Andrew .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (29) :5485-5497

← 1 2 3 4 5 →