Lewis and Bronsted acid catalyzed allylboration of carbonyl compounds: From discovery to mechanism and applications

被引：176

作者：

Hall, Dennis G. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

SYNLETT | 2007年 / 11期

关键词：

allylations; boron; catalysis; Lewis acids; stereoselectivity;

D O I：

10.1055/s-2007-980384

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The recent development of Lewis and Bronsted acid catalyzed manifolds for the allylboration of carbonyl compounds has opened doors towards an ideal carbonyl allylation methodology using stable and nontoxic allylic boronates as reagents. This Account relates our laboratory's discovery of acid-catalyzed allylborations, mechanistic investigations of these new processes, arid ongoing efforts by our group and others towards a general catalytic enantioselective allylboration methodology.

引用

页码：1644 / 1655

页数：12

共 72 条

[1] Protonated chiral catalysts: Versatile tools for asymmetric synthesis [J].

Bolm, C ;

Rantanen, T ;

Schiffers, I ;

Zani, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1758-1763

[2] ENANTIOMERIC (Z)-CROTYLDIISOPINOCAMPHEYLBORANE AND (E)-CROTYLDIISOPINOCAMPHEYLBORANE - SYNTHESIS IN HIGH OPTICAL PURITY OF ALL 4 POSSIBLE STEREOISOMERS OF BETA-METHYLHOMOALLYL ALCOHOLS [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (02) :293-294

[3] ORGANOBORANES .53. A HIGH-FIELD VARIABLE-TEMPERATURE H-1 AND B-11 NMR-STUDY OF THE EFFECTS OF SOLVENT AND STRUCTURE ON REACTIVITY IN ALLYLBORATION [J].

BROWN, HC ;

RACHERLA, US ;

PELLECHIA, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1868-1874

[4] ASYMMETRIC CARBON CARBON BOND FORMATION VIA BETA-ALLYLDIISOPINOCAMPHEYLBORANE - SIMPLE SYNTHESIS OF SECONDARY HOMOALLYLIC ALCOHOLS WITH EXCELLENT ENANTIOMERIC PURITIES [J].

BROWN, HC ;

JADHAV, PK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2092-2093

[5] Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes [J].

Burgos, CH ;

Canales, E ;

Matos, K ;

Soderquist, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8044-8049

[6] B-allyl-10-Ph-9-borabicyclo[3.3.2]decanes:: Strategically designed for the asymmetric allylboration of ketones [J].

Canales, E ;

Prasad, KG ;

Soderquist, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11572-11573

[7] Additions of functionalized α-substituted allylboronates to aldehydes under the novel Lewis and Bronsted acid catalyzed manifolds [J].

Carosi, L ;

Lachance, H ;

Hall, DG .

TETRAHEDRON LETTERS, 2005, 46 (52) :8981-8985

[8] CONSTITUENTS OF EUPOMATIA SPECIES .14. THE STRUCTURES OF EUPOMATILONE-1, EUPOMATILONE-2, EUPOMATILONE-3, EUPOMATILONE-4, EUPOMATILONE-5, EUPOMATILONE-6 AND EUPOMATILONE-7 ISOLATED FROM EUPOMATIA-BENNETTII [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (12) :1705-1714

[9] CONSTITUENTS OF EUPOMATIA SPECIES .12. ISOLATION OF CONSTITUENTS OF THE TUBERS AND AERIAL PARTS OF EUPOMATIA-BENNETTII AND DETERMINATION OF THE STRUCTURES OF NEW ALKALOIDS FROM THE AERIAL PARTS OF E-BENNETTII AND MINOR ALKALOIDS OF E-LAURINA [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (11) :1615-1626

[10] Total synthesis of eupomatilones 4 and 6: Structurally rearranged and atropisomerically fluxional lignan natural products [J].

Coleman, RS ;

Gurrala, SR .

ORGANIC LETTERS, 2004, 6 (22) :4025-4028

← 1 2 3 4 5 6 7 8 →