Diastereoselective Construction of Functionalized Homoallylic Alcohols by Ni-Catalyzed Diboron-Promoted Coupling of Dienes and Aldehydes

被引：83

作者：

Cho, Hee Yeon ^{[1
]}

Morken, James P. ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 48期

关键词：

D O I：

10.1021/ja806113v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. This reductive Coupling furnishes an allyl boronic ester as the reaction product, a Compound which was readily converted to the derived allylic alcohol by oxidative workup.

引用

页码：16140 / +

页数：3

共 62 条

[1] TRANSITION-METAL-CATALYZED DIBORATION OF VINYLARENES [J].

BAKER, RT ;

NGUYEN, P ;

MARDER, TB ;

WESTCOTT, SA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (12) :1336-1338

[2] Platinum-catalyzed tandem diboration/intramolecular allylboration: Diastereoselective access to cyclohexanes bearing 1,3-diols [J].

Ballard, CE ;

Morken, JP .

SYNTHESIS-STUTTGART, 2004, (09) :1321-1324

[3] Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes [J].

Beletskaya, Irina ;

Moberg, Christina .

CHEMICAL REVIEWS, 2006, 106 (06) :2320-2354

[4] Platinum catalysed 3,4- and 1,4-diboration of α,β-unsaturated carbonyl compounds using bis-pinacolatodiboron [J].

Bell, NJ ;

Cox, AJ ;

Cameron, NR ;

Evans, JSO ;

Marder, TB ;

Duin, MA ;

Elsevier, CJ ;

Baucherel, X ;

Tulloch, AAD ;

Tooze, RP .

CHEMICAL COMMUNICATIONS, 2004, (16) :1854-1855

[5] Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene [J].

Bower, John F. ;

Patman, Ryan L. ;

Krische, Michael J. .

ORGANIC LETTERS, 2008, 10 (05) :1033-1035

[6] Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis [J].

Burks, Heather E. ;

Morken, James P. .

CHEMICAL COMMUNICATIONS, 2007, (45) :4717-4725

[7] Development, mechanism, and scope of the palladium-catalyzed enantioselective allene diboration [J].

Burks, Heather E. ;

Liu, Shubin ;

Morken, James P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (28) :8766-8773

[8] Platinum-catalysed 1,4-diboration of 1,3-dienes [J].

Clegg, W ;

Johann, TRF ;

Marder, TB ;

Norman, NC ;

Orpen, AG ;

Peakman, TM ;

Quayle, MJ ;

Rice, CR ;

Scott, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (09) :1431-1438

[9] Molecular orbital study of the mechanism of platinum(0)-catalyzed alkene and alkyne diboration reactions [J].

Cui, Q ;

Musaev, DG ;

Morokuma, K .

ORGANOMETALLICS, 1997, 16 (07) :1355-1364

[10] Rhodium catalysed diboration of unstrained internal alkenes and a new and general route to zwitterionic [L2Rh(η6-catBcat)] (cat = 1,2-O2C6H4) complexes [J].

Dai, CY ;

Robins, EG ;

Scott, AJ ;

Clegg, W ;

Yufit, DS ;

Howard, JAK ;

Marder, TB .

CHEMICAL COMMUNICATIONS, 1998, (18) :1983-1984

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