Enantioselective reductive coupling of alkynes and α-keto aldehydes via rhodium-catalyzed hydrogenation:: An approach to bryostatin substructures

被引：38
|
作者：
Cho, CW [1 ]
Krische, MJ [1 ]
机构：
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 05期
关键词：
D O I：
10.1021/ol052976s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides (x-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.
引用
收藏
页码：891 / 894
页数：4
相关论文
共 50 条
  • [11] Rhodium-Catalyzed Enantioselective Hydrogenation of Oxime Acetates
    Huang, Kexuan
    Li, Shengkun
    Chang, Mingxin
    Zhang, Xumu
    ORGANIC LETTERS, 2013, 15 (03) : 484 - 487
  • [12] Enantioselective reductive coupling of 1,3-enynes to heterocyclic aromatic aldehydes and ketones via rhodium-catalyzed asymmetric hydrogenation: Mechanistic insight into the role of Bronsted acid additives
    Komanduri, Venukrishnan
    Krische, Michael J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) : 16448 - 16449
  • [13] Rhodium-catalyzed hydroformylation of internal alkynes to α,β-unsaturated aldehydes
    Angew Chem (Int Ed Engl), 16 (1760-1761):
  • [14] Rhodium-catalyzed addition of alkynes to activated ketones and aldehydes
    Dhondi, PK
    Chisholm, JD
    ORGANIC LETTERS, 2006, 8 (01) : 67 - 69
  • [15] Rhodium-catalyzed enantioselective reductive aldol reaction.
    Duffey, MO
    Taylor, SJ
    Morken, JP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U123 - U123
  • [16] Rhodium-Catalyzed Coupling Reaction of Salicyl Aldehydes with Alkynes via Cleavage of the Aldehyde C-H Bond
    Kokubo, K.
    Matsumasa, K.
    Miura, M.
    Nomura, M.
    Journal of Organic Chemistry, 62 (14):
  • [17] Rhodium-catalyzed coupling reaction of salicyl aldehydes with alkynes via cleavage of the aldehyde C-H bond
    Kokubo, K
    Matsumasa, K
    Miura, M
    Nomura, M
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14): : 4564 - 4565
  • [18] Rhodium-Catalyzed Addition of α-Keto Acid Chlorides with Terminal Alkynes
    Kashiwabara, Taigo
    Tanaka, Masato
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (09) : 1485 - 1490
  • [19] Highly enantioselective rhodium-catalyzed hydrogenation with monodentate ligands
    van den Berg, M
    Minnaard, AJ
    Schudde, EP
    van Esch, J
    de Vries, AHM
    de Vries, JG
    Feringa, BL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11539 - 11540
  • [20] Rhodium-Catalyzed Highly Enantioselective Hydrogenation of a Tetrasubstituted Enamine
    Yamada, Masatoshi
    Kato, Tomoaki
    Ikemoto, Tomomi
    Yamano, Mitsuhisa
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2021, 25 (04) : 1074 - 1079
12345