Stereospecific β-lithiation of oxazolinyloxiranes:: Synthesis of α,β-epoxy-γ-butyrolactones

被引:43
作者
Capriati, V [1 ]
Degennaro, L [1 ]
Favia, R [1 ]
Florio, S [1 ]
Luisi, R [1 ]
机构
[1] Univ Bari, Dipartimento Farmaco Chim, ICCOM, I-70125 Bari, Italy
关键词
D O I
10.1021/ol025781i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereospecific beta-lithlation of beta-aryl-substituted oxazollnyloxiranes is described. The trapping reaction of such reactive intermediates with carbonyl compounds gave alpha,beta-epoxy-gamma-butyrolactones after deblocking of the oxazoline moiety. This methodology has been also extended to the synthesis of optically active alpha,beta-epoxy-gamma-butyrolactones.
引用
收藏
页码:1551 / 1554
页数:4
相关论文
共 14 条
[1]   A stereospecific synthesis of oxazolinyloxiranes [J].
Abbotto, A ;
Capriati, V ;
Degennaro, L ;
Florio, S ;
Luisi, R ;
Pierrot, M ;
Salomone, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3049-3058
[2]  
Capriati V, 2001, EUR J ORG CHEM, V2001, P2035, DOI 10.1002/1099-0690(200106)2001:11<2035::AID-EJOC2035>3.0.CO
[3]  
2-R
[4]  
Capriati V, 2001, SYNTHESIS-STUTTGART, P2299
[5]   NOVEL (ALPHA-BETA-EPOXYALKYL)LITHIUM REAGENTS VIA THE LITHIATION OF ORGANYL-SUBSTITUTED EPOXIDES [J].
EISCH, JJ ;
GALLE, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4835-4840
[6]   On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds [J].
Florio, S ;
Capriati, V ;
Luisi, R ;
Abbotto, A ;
Pippel, DJ .
TETRAHEDRON, 2001, 57 (31) :6775-6786
[7]  
HASSNER A, 1985, CHEM HETEROCYCLIC CO, P10
[8]  
*IUPAC, 1979, NOM ORG CHEM A, P482
[9]   3JCH COUPLING-CONSTANTS IN OXIRANES, THIIRANES, AND CYCLOPROPANES [J].
KINGSBURY, CA ;
DURHAM, DL ;
HUTTON, R .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (25) :4696-4700
[10]   Generation and reaction of an oxiranyl anion derived from α,β-epoxy-γ-butyrolactone [J].
Kuramochi, K ;
Itaya, H ;
Nagata, S ;
Takao, K ;
Kobayashi, S .
TETRAHEDRON LETTERS, 1999, 40 (41) :7367-7370