Competing Domino Processes: Path-Discriminating Ability of Epoxide Stereochemistry at the Angular Position

被引:10
作者
Aquino, Maurizio [1 ]
Safir, Imad [1 ]
Elkhayat, Zobida [1 ]
Gandara, Zoila [1 ]
Perez, Manuel [1 ]
Retailleau, Pascal [1 ]
Arseniyadis, Simeon [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
MOLECULAR COMPLEXITY; POLYCYCLIC ETHERS; CYCLOADDITIONS; SUBSTITUTION; CYCLIZATION;
D O I
10.1021/ol9013377
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Structurally different products can be reached selectively from unsaturated vicinal bicyclic diols, which differ only by the epoxide configuration at the angular position. It is possible to modify the regiochemical outcome of the domino process in such a way as to create a different pathway, [4 + 2] versus [4 + 3 + 2], and control product distribution by using the configuration bias. No previous example of a domino variant of the [4 + 3 + 2] process appears to have been documented.
引用
收藏
页码:3610 / 3613
页数:4
相关论文
共 24 条
[1]  
Criegee R., 1965, OXIDATION ORGANIC A, P277
[2]  
de la Hoz A, 2000, EUR J ORG CHEM, V2000, P3659
[3]   Microwave-accelerated competing domino processes: A tether-controlled dual pathway into high molecular complexity [J].
Elkhayat, Zobida ;
Safir, Imad ;
Castellote, Isabel ;
Retailleau, Pascal ;
Arseniyadis, Simeon .
ORGANIC LETTERS, 2008, 10 (11) :2219-2222
[4]   Exploring modular domino reactions: Competing processes based on the nature of the angular substituent [J].
Elkhayat, Zobida ;
Safir, Imad ;
Retailleau, Pascal ;
Arseniyadis, Simeon .
ORGANIC LETTERS, 2007, 9 (23) :4841-4844
[5]   Microwave-Assisted Competing Domino Processes in the Octaline Diol Series [J].
Elkhayat, Zobida ;
Safir, Imad ;
Aquino, Maurizio ;
Perez, Manuel ;
Gandara, Zoila ;
Retailleau, Pascal ;
Arseniyadis, Simeon .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (16) :2687-2694
[6]   Recent advances in the synthesis of trans-fused polycyclic ethers by hydroxy-epoxide-cyclization and ether-ring-expansion reactions [J].
Fujiwara, K ;
Murai, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (12) :2129-2146
[7]   The impact of microwave synthesis on drug discovery [J].
Kappe, CO ;
Dallinger, D .
NATURE REVIEWS DRUG DISCOVERY, 2006, 5 (01) :51-63
[8]  
Kappe CO, 2005, METH PRIN MED CHEM, V52, P1, DOI 10.1002/3527606556
[9]   Oxidatively generated electrophiles as initiators of epoxide cascade cyclization processes [J].
Kumar, VS ;
Wan, SY ;
Aubele, DL ;
Floreancig, PE .
TETRAHEDRON-ASYMMETRY, 2005, 16 (21) :3570-3578
[10]   COBALT-CATALYZED [2-PI+2-PI+2-PI] (HOMO DIELS-ALDER) AND [2-PI+2-PI+4-PI] CYCLOADDITIONS OF BICYCLO[2.2.1]HEPTA-2,5-DIENES [J].
LAUTENS, M ;
TAM, W ;
LAUTENS, JC ;
EDWARDS, LG ;
CRUDDEN, CM ;
SMITH, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (26) :6863-6879