Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using triphenylphosphoranylideneketene (the bestmann ylide) and their use in Wittig reactions

被引:11
作者
Boeckman, Robert K., Jr. [1 ]
Song, Xinyi [1 ]
Pero, Joseph E. [1 ]
机构
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
关键词
D O I
10.1021/jo061732y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Camphor-derived lactams and other related chiral controllers have been found to react with the Bestmann ylide (triphenyl-phosphoranylideneketene) upon heating in toluene. The resulting parent ylides provide convenient access to a structurally diverse set of chiral stabilized ylides via functionalization. The utility of these chiral ylides for Wittig reactions has been briefly investigated and the effects of alpha-substitution noted.
引用
收藏
页码:8969 / 8972
页数:4
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共 45 条
[1]  
Abell A. D., 2004, Organophosphorus Reagents, P99
[2]   Diastereoselective chelation-controlled radical cyclization of chiral oxazolidinone-derived 2-alkenamides and modeling of the transition state [J].
Badone, D ;
Bernassau, JM ;
Cardamone, R ;
Guzzi, U .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (05) :535-538
[3]  
Bestmann H.J., 1976, ANGEW CHEM, V88, P92, DOI DOI 10.1002/ANGE.19760880311
[4]  
Bestmann H.J., 1985, ANGEW CHEM, V97, P783
[5]  
BESTMANN HJ, 1994, SYNTHESIS-STUTTGART, P1257
[6]  
BESTMANN HJ, 1960, TETRAHEDRON LETT, P5
[7]   CUMULATED YLIDES .7. A METHOD FOR THE SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBOXYLIC COMPOUNDS [J].
BESTMANN, HJ ;
SCHMID, G ;
SANDMEIER, D .
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (03) :912-918
[8]   CUMULATED YLIDES .6. NEW SYNTHESIS OF "(TRIPHENYLPHOSPHORANYLIDENE)KETENE, ITS THIO ANALOG, AND STABLE PROPADIENYLIDENETRIPHENYLPHOSPHORANES [J].
BESTMANN, HJ ;
SANDMEIER, D .
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (01) :274-277
[9]  
BESTMANN HJ, 1979, CARBON CARBON BOND F, V1, P353
[10]   Toward the development of a general chiral auxiliary .5. High diastereofacial selectivity in cycloadditions with trienol silyl ethers: An application to an enantioselective synthesis of (-)-cassioside [J].
Boeckman, RK ;
Liu, YG .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7984-7985