Enantioselective catalytic formation of quaternary stereogenic centers

被引:496
作者
Cozzi, Pier Giorgio [1 ]
Hilgraf, Robert [2 ]
Zimmermann, Nicole [3 ]
机构
[1] Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Celgene Corp, San Diego, CA 92121 USA
[3] Vertex Pharmaceut Inc, San Diego, CA 92121 USA
关键词
quaternary stereocenters; catalysis; synthetic methods; ketones; tertiary alcohols;
D O I
10.1002/ejoc.200700318
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantio selective catalytic formation of tertiary stereogenic centers has nowadays reached an impressive level of maturity, as is reflected in the large variety of available methods that afford high yields and high stereoselectivities. However, the development of stereoselective approaches for the formation of quaternary stereogenic centers still represents an enormous challenge for synthetic chemists. On the other hand, biologically active molecules containing quaternary stereogenic centers provide an incentive for the development of new, selective, and useful processes. Over the last few years, breakthrough work relating to the formation of fully substituted carbon centers has appeared in the literature. In this review we discuss recent highlights of this new direction in catalysis research: the formation of quaternary stereogenic centers by enantioselective catalytic methodologies. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007.
引用
收藏
页码:5969 / 5994
页数:26
相关论文
共 283 条
  • [1] AKIYAMA T, 1994, SYNLETT, P275
  • [2] New polymer-supported catalysts derived from Cinchona alkaloids:: Their use in the asymmetric Michael reaction
    Alvarez, R
    Hourdin, MA
    Cavé, C
    d'Angelo, J
    Chaminade, P
    [J]. TETRAHEDRON LETTERS, 1999, 40 (39) : 7091 - 7094
  • [3] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
    Anand, NK
    Carreira, EM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) : 9687 - 9688
  • [4] [Anonymous], 2005, ANGEW CHEM
  • [5] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B
    Austin, JF
    Kim, SG
    Sinz, CJ
    Xiao, WJ
    MacMillan, DWC
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5482 - 5487
  • [6] Insight into the mechanism of the asymmetric addition of alkyl groups to aldehydes catalyzed by titanium - BINOLate species
    Balsells, J
    Davis, TJ
    Carroll, P
    Walsh, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10336 - 10348
  • [7] α,β-unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions:: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor
    Balskus, Emily P.
    Jacobsen, Eric N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6810 - 6812
  • [8] Bartoli G, 2006, ANGEW CHEM, V118, P5088, DOI DOI 10.1002/ange.200600370
  • [9] Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides
    Bartoli, Giuseppe
    Bosco, Marcella
    Carlone, Armando
    Cavalli, Andrea
    Locatelli, Manuela
    Mazzanti, Andrea
    Ricci, Paolo
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) : 4966 - 4970
  • [10] ALDOL CONDENSATION OF EVANS CHIRAL ENOLATES WITH ACETOPHENONES - ITS APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF HOMOCHIRAL ANTIFUNGAL AGENTS
    BARTROLI, J
    TURMO, E
    BELLOC, J
    FORN, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) : 3000 - 3012