Highly Convergent Synthesis of Chiral Bicyclophosphinates by Domino Hydrophosphinylation/Michael/Michael Reaction

被引:10
作者
Fourgeaud, Pierre [1 ]
Dayde, Benedicte [1 ]
Volle, Jean-Noel [1 ]
Vors, Jean-Pierre [2 ]
Van der Lee, Arie [3 ]
Pirat, Jean-Luc [1 ]
Virieux, David [1 ]
机构
[1] ENSCM, Inst Charles Gerhardt, UMR 5253, AM2N, F-34296 Montpellier, France
[2] Bayer CropSci SAS, F-69263 Lyon 09, France
[3] Univ Montpellier 2, IEM, F-34095 Montpellier 5, France
关键词
ENANTIOSELECTIVE HYDROPHOSPHONYLATION; CASCADE REACTIONS; PHOSPHINE OXIDES; ALLENYLPHOSPHONATES; DERIVATIVES; ALDEHYDES; PRECURSORS; CHEMISTRY; PRODUCTS; ALCOHOLS;
D O I
10.1021/ol2019345
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diastereoselective domino reactions of iminoalcohols and allenyl H-phosphinates produce chiral phosphorus bicycles in a regio- and stereoselective fashion. A predictive model for diastereoselection is used for these new chiral phosphinic esters.
引用
收藏
页码:5076 / 5079
页数:4
相关论文
共 48 条
[1]  
Belakhov V. V., 1985, J GEN CHEM USSR, V55, P39
[2]   TOTAL SYNTHESIS OF THE UNUSUAL MARINE ALKALOID (-)-PAPUAMINE UTILIZING A NOVEL IMINO ENE REACTION [J].
BORZILLERI, RM ;
WEINREB, SM ;
PARVEZ, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :10905-10913
[3]   Synthesis and molecular structure of new unsaturated analogues of nucleotides containing six-membered rings [J].
Brel, VK ;
Belsky, VK ;
Stash, AI ;
Zavodnik, VE ;
Stang, PJ .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (03) :512-521
[4]   ALPHA-PHENYLGLYCINOL AS CHIRAL AUXILIARY IN DIASTEREOSELECTIVE STRECKER SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
CHAKRABORTY, TK ;
HUSSAIN, KA ;
REDDY, GV .
TETRAHEDRON, 1995, 51 (33) :9179-9190
[5]   Reactivity and utility of allenylphosphonates: Formation of a novel hydroperoxide and propargylic alcohol and facile thiol addition under catalyst-free, solvent-free conditions [J].
Chakravarty, Manab ;
Swamy, K. C. Kumara .
SYNTHESIS-STUTTGART, 2007, (20) :3171-3178
[6]   Allenylphosphonates - Useful precursors of pyrazoles and 1,2,3-triazoles [J].
Chakravarty, Manab ;
Kumar, N. N. Bhuvan ;
Sajna, K. V. ;
Swamy, K. C. Kumara .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (26) :4500-4510
[7]   First syntheses of 2-hydrogeno-2-oxo-1,4,2-oxazaphosphinanes via intramolecular esterification [J].
Cristau, HJ ;
Monbrun, J ;
Tillard, M ;
Pirat, JL .
TETRAHEDRON LETTERS, 2003, 44 (15) :3183-3186
[8]   4-Phenylsulfenyl- and 4-Phenylselenenyl-2,5-dihydro-1,2-oxaphosphole-2-oxides by the Reaction of 1,2-Alkadienephosphonic Amidoesters with Sulphenyl- and Selenenylbromides [J].
Enchev, D. D. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (11) :2649-2654
[9]  
Enchev DD, 2005, PHOSPHORUS SULFUR, V180, P2127, DOI 10.1080/104265090917628
[10]   Asymmetric organocatalytic domino reactions [J].
Enders, Dieter ;
Grondal, Christoph ;
Huettl, Matthias R. M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581