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

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作者
Lee, CW
Gil, JM
Oh, DY
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O62 [有机化学];
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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.
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页码:943 / 948
页数:6
相关论文
共 22 条
[11]   T-BUOK-INDUCED CLEAVAGE OF DIHYDROFURAN DERIVATIVES - SYNTHESIS OF BETA-(DIETHOXYPHOSPHINYL)-BETA,GAMMA-UNSATURATED KETONES [J].
LEE, CW ;
HONG, JE ;
OH, DY .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :7027-7029
[12]  
Lee CW, 1996, HETEROCYCLES, V43, P1171
[13]  
LEE KS, 1989, B KOR CHEM SOC, V10, P613
[14]   A CONVENIENT STEREOSELECTIVE SYNTHESIS OF FLUORINATED ALPHA-ALKYLIDENE-GAMMA-BUTYROLACTONE DERIVATIVES [J].
LU, XY ;
WANG, Z ;
JI, JU .
TETRAHEDRON LETTERS, 1994, 35 (04) :613-616
[15]  
LU XY, 1993, SYNLETT, P68
[16]  
McGraw W. J., 1953, [No title captured], Patent No. [2624723, US2624723A]
[17]   REACTIONS OF AN "ALPHA-PHOSPHONO-GAMMA-BUTYROLACTONE CARBANION WITH ACID ANHYDRIDES, EPOXIDES, CARBONATES, AND A LACTONE [J].
MINAMI, T ;
MATSUMOTO, M ;
SUGANUMA, H ;
AGAWA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) :2149-2153
[18]   SYNTHESIS OF ALPHA-YLIDENE-GAMMA-BUTYROLACTONES USING AN "ALPHA-PHOSPHONO-GAMMA-BUTYROLACTONE CARBANION [J].
MINAMI, T ;
NIKI, I ;
AGAWA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (22) :3236-3238
[19]  
PETRAGNANI N, 1986, J ORG CHEM, P157
[20]   PALLADIUM(II)-CATALYZED CARBONYLATION OF 3-BUTEN-1-OLS AND 3-BUTYN-1-OLS - AN EFFICIENT SYNTHESIS OF GAMMA-BUTYROLACTONES [J].
TAMARU, Y ;
HOJO, M ;
YOSHIDA, Z .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1099-1105