Synthetic route to alpha-phosphono-gamma-butyrolactones: Synthesis of gamma-substituted alpha-methylene-gamma-butyrolactones

被引:0
作者
Lee, CW
Gil, JM
Oh, DY
机构
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of lithiated homoallylic phosphonates with dimethyl carbamyl chloride gave 2-amidophosphonate derivatives. A solution of 2-amidophosphonate in DME-H2O (2:1 vol) reacted with 2 eq. iodine at room temperature to give alpha-phosphono-gamma-iodoalkyl-gamma-butyrolactones in good yield, although the products are mixture. Wadsworth-Emmons reaction of alpha-phosphono-gamma-iodoalkyl-gamma-butyrolactones with aldehydes gave alpha-(alkyl)methylene-gamma-iodoalkyl-gamma-butyro-lactone derivatives.
引用
收藏
页码:943 / 948
页数:6
相关论文
共 22 条
[1]  
BUECHEL KH, 1965, LIEBIGS ANN CHEM, V685, P10
[2]   A NEW APPROACH TO THE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-BUTYROLACTONES [J].
CARLSON, RM ;
YANG, Q .
TETRAHEDRON LETTERS, 1994, 35 (43) :7919-7922
[3]   ALLENYL ETHERS AS PRECURSORS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES AND BOTRYODIPLODIN DERIVATIVES [J].
DULCERE, JP ;
MIHOUBI, MN ;
RODRIGUEZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5709-5716
[4]   PRACTICAL SYNTHESIS OF "ALPHA-METHYLENE-GAMMA-BUTYROLACTONE [J].
GRIECO, PA ;
POGONOWS.CS .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13) :1958-1959
[5]  
GRIECO PA, 1975, SYNTHESIS-STUTTGART, P67
[6]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].
HOFFMANN, HMR ;
RABE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110
[7]  
HUTCHINS.CR, 1974, J ORG CHEM, V39, P1854, DOI 10.1021/jo00927a015
[8]   SYNTHESIS OF ALPHA-PHOSPHONO LACTONES AND ESTERS THROUGH A VINYL PHOSPHATE PHOSPHONATE REARRANGEMENT [J].
JACKSON, JA ;
HAMMOND, GB ;
WIEMER, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4750-4754
[9]  
JI JG, 1993, SYNLETT, P745
[10]   A FACILE SYNTHESIS OF 2,4-DISUBSTITUTED FURANS FROM BETA-HYDROXY SULFONES [J].
JUNG, JH ;
LEE, JW ;
OH, DY .
TETRAHEDRON LETTERS, 1995, 36 (06) :923-926