First stereoselective inverse demand [4+2] cycloaddition reactions of novel chiral allenamides with heterodienes. Preparation of highly functionalized 5-arylpyranyl heterocycles

被引:61
作者
Wei, LL [1 ]
Hsung, RP [1 ]
Xiong, H [1 ]
Mulder, JA [1 ]
Nkansah, NT [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol990345q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first stereoselective inverse demand [4 + 2] cycloaddition reactions of chiral allenamides with heterodienes are described here. These reactions lead to stereoselective synthesis of highly functionalized pyranyl heterocycles. A mechanistic model is also proposed here based on the stereochemical assignment and comparisons of stereoselectivities obtained from various chiral allenamides.
引用
收藏
页码:2145 / 2148
页数:4
相关论文
共 28 条
[21]   SOME REACTIONS OF N-PROPADIENYL-4-QUINOLONES [J].
RADL, S ;
KOVAROVA, L .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1991, 56 (11A) :2413-2419
[22]   ACETYLENIC CHEMISTRY .12. PHASE-TRANSFER-CATALYZED REACTION OF 9(10H)-ACRIDINONE WITH ALKYNYL HALIDES [J].
REISCH, J ;
SALEHIARTIMANI, RA .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (06) :1803-1806
[23]  
Saalfrank R. W., 1993, METHODEN ORGANISCHEN, P3093
[24]  
Schuster H.F., 1984, ALLENES ORGANIC SYNT
[25]   A NEW CHIRAL OXAZOLIDINONE DERIVED FROM DIPHENYLALANINOL - ALDOL, ALKYLATION, AND DIELS-ALDER REACTIONS [J].
SIBI, MP ;
DESHPANDE, PK ;
JI, JG .
TETRAHEDRON LETTERS, 1995, 36 (49) :8965-8968
[26]   Acyclic stereocontrol in radical reactions: rho-selectivity with oxazolidinone auxiliaries [J].
Sibi, MP ;
Ji, JG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02) :190-192
[27]   Enantioselective free radical reactions [J].
Sibi, MP ;
Porter, NA .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (02) :163-171
[28]   Inverse demand [4+2] cycloaddition reactions of allenamides: reactivity scopes of an electron deficient variant of allenamines [J].
Wei, LL ;
Xiong, H ;
Douglas, CJ ;
Hsung, RP .
TETRAHEDRON LETTERS, 1999, 40 (38) :6903-6907