Synthesis of Optically Active β- or γ-Alkyl-Substituted Alcohols through Copper-Catalyzed Asymmetric Allylic Alkylation with Organolithium Reagents

被引:18
作者
Guduguntla, Sureshbabu [1 ]
Fananas-Mastral, Martin [1 ]
Feringa, Ben L. [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
关键词
ENANTIOSELECTIVE SYNTHESIS; PHOSPHORAMIDITE LIGAND; CARBOALUMINATION; ALDEHYDES; ALKENES;
D O I
10.1021/jo401536u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot synthesis of optically active beta-alkyl-substituted alcohols through a tandem copper-catalyzed asymmetric allylic alkylation (AAA) with organolithium reagents and reductive ozonolysis is presented. Furthermore, hydroboration-oxidation following the Cu-catalyzed AAA leads to the corresponding homochiral gamma-alkyl-substituted alcohols.
引用
收藏
页码:8274 / 8280
页数:7
相关论文
共 43 条
[1]   Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].
Alexakis, A. ;
Backvall, J. E. ;
Krause, N. ;
Pamies, O. ;
Dieguez, M. .
CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823
[2]   Enantioselective α-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4260-4263
[3]   An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation [J].
Burk, MJ ;
de Koning, PD ;
Grote, TM ;
Hoekstra, MS ;
Hoge, G ;
Jennings, RA ;
Kissel, WS ;
Le, TV ;
Lennon, IC ;
Mulhern, TA ;
Ramsden, JA ;
Wade, RA .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) :5731-5734
[4]   Total Synthesis of Danshenspiroketallactone [J].
Chorley, Daniel F. ;
Chen, Jack Li-Yang ;
Furkert, Daniel P. ;
Sperry, Jonathan ;
Brimble, Margaret A. .
SYNLETT, 2012, 23 (01) :128-130
[5]   Diastereoselective Thia-Claisen rearrangement of pyrrolidinone-derived ketene N,S-acetals [J].
Ellwood, Adam R. ;
Mortimer, Anne J. Price ;
Tocher, Derek A. ;
Porter, Michael J. .
SYNLETT, 2008, (14) :2199-2203
[6]   Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite-Catalyzed Allylic Alkylation with Organolithium Reagents [J].
Fananas-Mastral, Martin ;
Perez, Manuel ;
Bos, Pieter H. ;
Rudolph, Alena ;
Harutyunyan, Syuzanna R. ;
Feringa, Ben L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (08) :1922-1925
[7]   Total Synthesis of the Anti-Apoptotic Agents Iso- and Bongkrekic Acids [J].
Francais, Antoine ;
Leyva, Antonio ;
Etxebarria-Jardi, Gorka ;
Ley, Steven V. .
ORGANIC LETTERS, 2010, 12 (02) :340-343
[8]  
GEERDINK D, 2013, J CHEM SCI, V4, P709
[9]   Chiral N-heterocyclic carbenes in natural product synthesis: Application of Ru-catalyzed asymmetric ring-opening/cross-metathesis and Cu-catalyzed allylic alkylation to total synthesis of baconipyrone C [J].
Gillingham, Dennis G. ;
Hoveyda, Amir H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3860-3864
[10]   Highly Enantioselective α Alkylation of Aldehydes with 1,3-Benzodithiolylium Tetrafluoroborate: A Formal Organocatalytic α Alkylation of Aldehydes by the Carbenium Ion [J].
Gualandi, Andrea ;
Emer, Enrico ;
Capdevila, Montse Guiteras ;
Cozzi, Pier Giorgio .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (34) :7842-7846