Synthesis and structure of highly polarised double-bond compounds derived from S-proline

被引:4
作者
Aitken, RA [1 ]
Ali, K [1 ]
de Elena, N [1 ]
Lightfoot, P [1 ]
机构
[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
关键词
iminium salts; enamino esters; thiazolidines; X-ray crystal structures;
D O I
10.1016/S0040-4039(00)01372-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of the chiral iminium salt 3 with stabilised carbanions gives the compounds 4-9 containing a highly polarised double bond. The extent of this polarisation is determined by variable temperature H-1 NMR studies, comparison of C-13 NMR chemical shifts and an X-ray structure determination. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7965 / 7968
页数:4
相关论文
共 10 条
[1]   A POLARIZED, TWISTED, ETHYLENE - STRUCTURE OF METHYL 2-(1,3-DIMETHYL-2-IMIDAZOLIDINYLIDENE)-3-OXOBUTYRATE DIHYDRATE, C10H16N2O3.2H2O [J].
ADHIKESAVALU, D ;
VENKATESAN, K .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1983, 39 (OCT) :1424-1426
[3]  
Aitken RA, 1997, TETRAHEDRON LETT, V38, P4179
[4]  
[Anonymous], 1994, J CHEM RES M, P1001
[6]   ASYMMETRIC-SYNTHESIS BASED ON CHIRAL DIAMINES HAVING PYRROLIDINE RING [J].
MUKAIYAMA, T .
TETRAHEDRON, 1981, 37 (23) :4111-4119
[7]   STATIC AND DYNAMIC STEREOCHEMISTRY OF PUSH-PULL AND STRAINED ETHYLENES [J].
SANDSTROM, J .
TOPICS IN STEREOCHEMISTRY, 1983, 14 :83-181
[8]   NMR INVESTIGATION OF ROTATION ABOUT CARBON-CARBON DOUBLE-BOND - KINETIC AND THERMODYNAMIC ASPECTS OF ISOMERIZATION OF CONJUGATED KETENE-MERCAPTOAMINALS [J].
SHVO, Y ;
BELSKY, I .
TETRAHEDRON, 1969, 25 (19) :4649-&
[9]   STUDIES OF POLARIZED ETHYLENES .4. BARRIERS TO ROTATION AROUND FORMAL DOUBLE-BONDS AND FORMAL SINGLE BONDS IN 1,1-BIS-DIMETHYLAMINOETHYLENES [J].
WENNERBECK, I ;
SANDSTROM, J .
ORGANIC MAGNETIC RESONANCE, 1972, 4 (06) :783-809
[10]  
YADAV LDS, 1992, INDIAN J CHEM B, V31, P604