Allylic alkylation versus Michael induced ring closure: Chelated enolates as versatile nucleophiles

被引:36
作者
Pohlman, M [1 ]
Kazmaier, U [1 ]
Lindner, T [1 ]
机构
[1] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany
关键词
D O I
10.1021/jo049036q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylic carbonates 8 bearing an electron-withdrawing ester functionality can act as substrates for palladium-catalyzed allylic alkylations or as Michael acceptors with the option to undergo subsequent ring closure. Chelated amino acid ester enolates 1' are versatile nucleophiles for both reactions giving high yields and selectivites.
引用
收藏
页码:6909 / 6912
页数:4
相关论文
共 46 条
[1]  
AKERMARK B, 1990, J AM CHEM SOC, V112, P4587
[2]   RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].
BUNCE, RA .
TETRAHEDRON, 1995, 51 (48) :13103-13159
[3]   Enantioselective synthesis of L-CCG-I [J].
Chavan, SP ;
Sharma, P ;
Sivappa, R ;
Bhadbhade, MM ;
Gonnade, RG ;
Kalkote, UR .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6817-6819
[4]   Study of the reactivity profile of glycine Schiff's bases with dipolarophiles: Application towards a concise synthesis of CCG-II [J].
Chavan, SP ;
Venkatraman, MS ;
Sharma, AK ;
Chittiboyina, AG .
TETRAHEDRON LETTERS, 1996, 37 (16) :2857-2858
[5]   ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES [J].
CONSIGLIO, G ;
WAYMOUTH, RM .
CHEMICAL REVIEWS, 1989, 89 (01) :257-276
[6]  
CORRADINI P, 1966, J CHEM SOC CHEM COMM, P618
[7]  
Godleslcy S., 1991, COMPREHENSIVE ORGANI, V4, P585
[8]  
Hegedus L.S., 1999, TRANSITION METALS SY, V2nd
[9]   STEREOSPECIFIC REDUCTION AND CROSS-COUPLING OF GAMMA-MONOSUBSTITUTED ALLYLIC CHLORIDES USING COORDINATIVELY UNSATURATED PALLADIUM CATALYSTS [J].
HUTZINGER, MW ;
OEHLSCHLAGER, AC .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2918-2920
[10]   REACTION OF SCHIFF-BASES ANIONS WITH 4-HALO-2-BUTENOATES - SELECTIVE SYNTHESIS OF ALPHA-CYCLOPROPYL AND GAMMA-UNSATURATED, DELTA-UNSATURATED ALPHA-AMINO-ACID DERIVATIVES [J].
JOUCLA, M ;
ELGOUMZILI, M ;
FOUCHET, B .
TETRAHEDRON LETTERS, 1986, 27 (15) :1677-1680