RADICAL CYCLIZATION OF BETA-ALLENIC HYDRAZONES - AN ASYMMETRIC APPROACH

被引:17
作者
BERNARDHENRIET, CD [1 ]
GRIMALDI, JR [1 ]
HATEM, JM [1 ]
机构
[1] UNIV AIX MARSEILLE 1,CNRS,CHIM ORGAN SYNTH LAB,F-13397 MARSEILLE 20,FRANCE
关键词
D O I
10.1016/S0040-4039(00)73075-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-allenic hydrazones undergo hydrostannylation to afford cyclopentene derivatives and linear rearranged products depending on the substitution of the allenic and hydrazone moieties. A first example of asymmetric radical cyclization of a SAMP beta-allenic hydrazone is described.
引用
收藏
页码:3699 / 3702
页数:4
相关论文
共 32 条
[1]   CYCLIZATIONS OF OMEGA-ALLENYL RADICALS [J].
APPARU, M ;
CRANDALL, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (12) :2125-2130
[2]   STEREOSELECTIVE RADICAL CYCLIZATION FOR THE SYNTHESIS OF BICYCLIC HIGHER-CARBON SUGARS - SYNTHESIS OF THE SUGAR MOIETY OF OCTOSYL ACIDS [J].
ARAKI, Y ;
ENDO, T ;
ARAI, Y ;
TANJI, M ;
ISHIDO, Y .
TETRAHEDRON LETTERS, 1989, 30 (21) :2829-2832
[3]  
ARMONE A, 1993, TETRAHEDRON, V49, P6873
[4]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].
BECKWITH, ALJ ;
SCHIESSER, CH .
TETRAHEDRON, 1985, 41 (19) :3925-3941
[5]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].
BECKWITH, ALJ .
TETRAHEDRON, 1981, 37 (18) :3073-3100
[6]   THE SYNTHESIS OF BICYCLIC AND TRICYCLIC RING-SYSTEMS BY RADICAL CYCLIZATION REACTIONS OF OXIME ETHERS [J].
BOOTH, SE ;
JENKINS, PR ;
SWAIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1248-1249
[7]   GENERATION OF AMINYL RADICALS USING SULFENAMIDES AS SYNTHETIC PRECURSORS [J].
BOWMAN, WR ;
CLARK, DN ;
MARMON, RJ .
TETRAHEDRON, 1994, 50 (04) :1275-1294
[8]   PYRROLIZIDINONE AND INDOLIZIDINONE SYNTHESIS - GENERATION AND INTRAMOLECULAR ADDITION OF ALPHA-ACYLAMINO RADICALS TO OLEFINS AND ALLENES [J].
BURNETT, DA ;
CHOI, JK ;
HART, DJ ;
TSAI, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (26) :8201-8209
[9]   REDUCTIVE CYCLIZATIONS OF ALLENIC KETONES BY DISSOLVING METALS [J].
CRANDALL, JK ;
MUALLA, M .
TETRAHEDRON LETTERS, 1986, 27 (20) :2243-2246
[10]  
DEMESMAEKER A, 1993, SYNLETT, P871