Enantioselective diethylzinc addition to aromatic and aliphatic aldehydes using (3R,5R)-dihydroxypiperidine derivatives catalyst

被引：62
|
作者：
Roudeau, R [1 ]
Pardo, DG [1 ]
Cossy, J [1 ]
机构：
[1] Ecole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, France
来源：
TETRAHEDRON | 2006年 / 62卷 / 10期
关键词：
enantioselective addition; aliphatic aldehydes; chiral ligands;
D O I：
10.1016/j.tet.2005.11.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of chiral (3R,5R)-dihydroxypiperidine derivatives 3a-f were conveniently prepared from trans-4-hydroxy-L-proline and applied to the catalytic enantioselective addition of diethylzinc to benzaldehyde and heptanal. Among them, 3d was found to show the best asymmetric induction in promoting the addition of Et2Zn to various aldehydes, providing (R)-secondary alcohols in up to 98% ee. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2388 / 2394
页数：7
相关论文
共 50 条
  • [41] Enantioselective addition of diethylzinc to aldehydes catalyzed by (R)-1-phenylethylamine-derived 1,4-amino alcohols
    Asami, Masatoshi
    Miyairi, Naomichi
    Sasahara, Yukihiro
    Ichikawa, Ken-ichi
    Hosoda, Naoya
    Ito, Suguru
    TETRAHEDRON, 2015, 71 (38) : 6796 - 6802
  • [42] Synthesis of enantiomerically pure (3R,4R,5R)-4-hydroxy isoleucine lactone
    Kassem, T
    Wehbe, J
    Rolland-Fulcrand, V
    Rolland, M
    Roumestant, ML
    Martinez, J
    TETRAHEDRON-ASYMMETRY, 2001, 12 (19) : 2657 - 2661
  • [43] BIOSYNTHESIS OF VERRUCARINS AND RORIDINS .4. MODE OF INCORPORATION OF (3R)-[(5R)-5-3H]-MEVALONATE INTO VERRUCAROL - EVIDENCE FOR IDENTITY OF C(11)-HYDROGEN ATOM OF TRICHOTHECANE SKELETON WITH (5R)-HYDROGEN ATOM OF (3R)-MEVALONIC ACID
    MULLER, B
    TAMM, C
    HELVETICA CHIMICA ACTA, 1975, 58 (02) : 483 - 488
  • [44] Synthesis of deuterium-labeled (3R, 5S)-fluvastatin and (3S, 5R)-fluvastatin
    He, Mei
    Li, Jian
    Tian, Lei
    JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY, 2019, 319 (01) : 263 - 269
  • [45] Synthesis of deuterium-labeled (3R, 5S)-fluvastatin and (3S, 5R)-fluvastatin
    Mei He
    Jian Li
    Lei Tian
    Journal of Radioanalytical and Nuclear Chemistry, 2019, 319 : 263 - 269
  • [46] An alternative synthetic strategy for (3R),(5R)-5-hydroxy-de-O-methyllasiodiplodin and its epimer
    Vema, Venkata Naresh
    Kumari, Y. Bharathi
    Musulla, Sridhar
    Addada, Rama Krishnam Raju
    Alapati, Srinivasa Rao
    TETRAHEDRON LETTERS, 2019, 60 (14) : 986 - 988
  • [47] [(3R*, 4R*, 5R*)-2,3-Diphenyl-isoxazolidine-4,5-diyl]dimethanol
    Guner, Selahaddin
    Seftalicioglu, Kubra
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2061 - +
  • [48] Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction
    Chakraborty, C
    Dhavale, DD
    CARBOHYDRATE RESEARCH, 2006, 341 (07) : 912 - 917
  • [49] THE BIOSYNTHETIC IMPLICATIONS OF ACETATE AND GLUTAMATE INCORPORATION INTO (3R,5R)-CARBAPENAM-3-CARBOXYLIC ACID AND (5R)-CARBAPEN-2-EM-3-CARBOXYLIC ACID BY SERRATIA SP
    BYCROFT, BW
    MASLEN, C
    BOX, SJ
    BROWN, A
    TYLER, JW
    JOURNAL OF ANTIBIOTICS, 1988, 41 (09): : 1231 - 1242
  • [50] A STEREOCONTROLLED SYNTHESIS OF (2R,3R,5R,13S,14R)-(+)-APLIDIASPHINGOSINE, A MARINE TERPENOID
    MORI, K
    UMEMURA, T
    TETRAHEDRON LETTERS, 1982, 23 (33) : 3391 - 3394
12345