Remarkably stable (Me3Al)2•DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes

被引:109
作者
Biswas, K [1 ]
Prieto, O [1 ]
Goldsmith, PJ [1 ]
Woodward, S [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词
aluminum; asymmetric catalysis; Lewis bases; nickel; phosphoramidites;
D O I
10.1002/anie.200462569
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Weigh it out in air! The DABAL reagent (Me3Al)2·(DABCO) (DABCO = 1,4-diazabicyclo[2.2.2] octane) can be easily handled under normal laboratory conditions. Furthermore, chiral secondary alcohols can be efficiently prepared from prochiral aldehydes (see scheme; TOF = turnover frequency) by using either DABAL or AIR3 reagents (R = Me, Et). Thus, DABAL can be used as an efficient, convenient alternative to the Schumann-Blum reagent. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2232 / 2234
页数:3
相关论文
共 25 条
[1]  
Baidossi W, 1996, SYNTHESIS-STUTTGART, P1127
[2]   Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
ORGANIC LETTERS, 1999, 1 (10) :1683-1686
[3]  
Blake AJ, 2000, CHEM-EUR J, V6, P3586, DOI 10.1002/1521-3765(20001002)6:19<3586::AID-CHEM3586>3.0.CO
[4]  
2-S
[5]   Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source [J].
Bolm, C ;
Rudolph, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14850-14851
[6]  
Börner C, 2001, EUR J ORG CHEM, V2001, P2435
[7]   INTERACTIONS OF 1,4-DIAZABICYCLO[2.2.2]OCTANE WITH GROUP-III METAL TRIMETHYLS - STRUCTURES OF ME3M.N(C2H4)3N.MME3 (M = AL, GA) [J].
BRADFORD, AM ;
BRADLEY, DC ;
HURSTHOUSE, MB ;
MOTEVALLI, M .
ORGANOMETALLICS, 1992, 11 (01) :111-115
[8]   P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis [J].
Colby, EA ;
Jamison, TF .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (01) :156-166
[9]   2,2′-bipyridine, 2-(2-oxazolyl)pyridine and 2,2′-bisoxazole derived nickel(0) complexes as selective catalysts for cross-coupling of aryl chlorides by intramolecularly stabilized dialkylaluminum reagents [J].
Gelman, D ;
Dechert, S ;
Schumann, H ;
Blum, J .
INORGANICA CHIMICA ACTA, 2002, 334 :149-158
[10]   1-Trifluoromethylvinylsilane as a CF2=C--CH2+ synthon:: Synthesis of functionalized 1,1-difluoro-1-alkenes via isolable 2,2-difluorovinylsilanes [J].
Ichikawa, J ;
Fukui, H ;
Ishibashi, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7800-7805