CHIRAL INDUCTION IN A FACILE THIO-CLAISEN REARRANGEMENT

被引:12
作者
REDDY, KV [1 ]
RAJAPPA, S [1 ]
机构
[1] NATL CHEM LAB,DIV ORGAN CHEM SYNTH,POONA 411008,MAHARASHTRA,INDIA
关键词
D O I
10.1016/S0040-4039(00)74788-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylation of nitrothioacetamides proceeds by initial S-allylation followed by an extremely facile thio-Claisen rearrangement. The diastereomeric excess in the allylation of N-nitrothioacetyl (L-)proline ethyl ester (4) is 66%.
引用
收藏
页码:7957 / 7960
页数:4
相关论文
共 16 条
[2]   STRUCTURES OF 2 ISOMERIC DIHYDROPYRIDINE DERIVATIVES WITH S-SUBSTITUENTS - SOLID-STATE ALLYL MIGRATION [J].
AUFDERHEYDE, TPE ;
BURGI, HB ;
SHKLOVER, VE .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :566-569
[3]  
BARTLETT PA, 1980, TETRAHEDRON, V36, P3
[4]  
BELSIN P, 1992, TETRAHEDRON, V48, P4135
[5]  
BENNETT GB, 1977, SYNTHESIS-STUTTGART, P589
[6]   DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ALLYLIC ALCOHOLS [J].
CHA, JK ;
LEWIS, SC .
TETRAHEDRON LETTERS, 1984, 25 (46) :5263-5266
[7]   ENANTIOSELECTIVE SYNTHESIS OF (-)-ELENOLIC ACID AND (-)-AJMALICINE [J].
HATAKEYAMA, S ;
SAIJO, K ;
TAKANO, S .
TETRAHEDRON LETTERS, 1985, 26 (07) :865-868
[8]  
HILL RK, 1964, TETRAHEDRON LETT, P3239
[9]   NITROKETENE-S,N-ACETALS AS PRECURSORS FOR NITROACETAMIDES AND THE ELUSIVE NITROTHIOACETAMIDES [J].
MANJUNATHA, SG ;
REDDY, KV ;
RAJAPPA, S .
TETRAHEDRON LETTERS, 1990, 31 (09) :1327-1330
[10]   FROM N-NITROACETYLPROLINE TO LEUCYLPROLINE [J].
MANJUNATHA, SG ;
RAJAPPA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) :372-373