Nucleophilic addition of triethyl phosphite to acetates of the Baylis-Hillman adducts: Stereoselective synthesis of (E)- and (Z)-allylphosphonates

被引：43

作者：

Basavaiah, D

Pandiaraju, S

机构：

[1] School of Chemistry, University of Hyderabad

来源：

TETRAHEDRON | 1996年 / 52卷 / 06期

关键词：

D O I：

10.1016/0040-4020(95)01055-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic addition of triethyl phosphite to 3-acetoxy-2-methylenealkanenitriles and methyl 3-acetoxy-2-methylenealkanoates provides (2E)-2-(diethoxyphosphorylmethyl)alk-2-enenitriles and methyl (2Z)-2-(diethoxyphosphorylmethyl) alk-2-enoates respectively with good stereoselectivity.

引用

页码：2261 / 2268

页数：8

共 16 条

[1] AMRI H, 1988, TETRAHEDRON LETT, V27, P4307
[2] PREPARATION AND NUCLEOPHILIC-SUBSTITUTION OF (E)-1-BROMO-2-PHENYLSULFONYL-2-ALKENES AND 3-ACETOXY-2-PHENYLSULFONYL-1-ALKENES
AUVRAY, P
KNOCHEL, P
NORMANT, JF
[J]. TETRAHEDRON, 1988, 44 (19) : 6095 - 6106
[3] A SIMPLE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXYALKANONES
BASAVAIAH, D
GOWRISWARI, VVL
[J]. TETRAHEDRON LETTERS, 1986, 27 (18) : 2031 - 2032
[4] FIRST ENANTIOSELECTIVE SYNTHESIS OF MIKANECIC ACID VIA DIELS-ALDER CYCLOADDITION MEDIATED CONSTRUCTION OF CHIRAL VINYLIC QUATERNARY CENTER
BASAVAIAH, D
PANDIARAJU, S
SARMA, PKS
[J]. TETRAHEDRON LETTERS, 1994, 35 (24) : 4227 - 4230
[5] APPLICATIONS OF THE BAYLIS-HILLMAN REACTION-2 - A SIMPLE STEREOSELECTIVE SYNTHESIS OF (E)-TRISUBSTITUTED AND (Z)-TRISUBSTITUTED ALKENES
BASAVAIAH, D
SARMA, PKS
BHAVANI, AKD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (09) : 1091 - 1092
[6] APPLICATIONS OF BAYLIS-HILLMAN COUPLING PRODUCTS - A REMARKABLE REVERSAL OF STEREOCHEMISTRY FROM ESTERS TO NITRILES - A SIMPLE SYNTHESIS OF (2E)-2-METHYLALK-2-EN-1-OLS AND (2Z)-2-METHYLALK-2-ENENITRILES
BASAVAIAH, D
SARMA, PKS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (13) : 955 - 957
[7] BASAVAIAH D, 1995, SYNLETT, P243
[8] THE JOHNSON-CLAISEN REARRANGEMENT OF 5-HYDROXY-2-METHYLENEALKANENITRILES - STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED TRISUBSTITUTED ALKENES
BASAVAIAH, D
PANDIARAJU, S
[J]. TETRAHEDRON LETTERS, 1995, 36 (05) : 757 - 758
[9] Baylis A. B, 1972, German Patent, Patent No. 2155113
[10] SYNTHESIS OF MONOPROTECTED 2-ALKYLIDENE-1,3-PROPANEDIOLS BY AN UNUSUAL SN2' MITSUNOBU REACTION
CHARETTE, AB
COTE, B
[J]. TETRAHEDRON LETTERS, 1993, 34 (43) : 6833 - 6836

← 1 2 →