Catalytic asymmetric Diels-Alder reactions of α-thioacrylates for the preparation of norbornenone

被引:31
作者
Aggarwal, VK [1 ]
Anderson, ES
Jones, DE
Obierey, KB
Giles, R
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
[2] SmithKline Beecham, Tonbridge TN11 9AN, Kent, England
关键词
D O I
10.1039/a805366i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cu-II-bisoxazoline complexes catalyse the asymmetric Diels-Alder cycloaddition of alpha-thioacrylates with cyclopentadiene to give the cycloadducts in up to 92% yield, 88% de and >95% ee for the endo product; deprotection gives good yields of (1S,4S)-norbornenone with high enantioselectivity.
引用
收藏
页码:1985 / 1986
页数:2
相关论文
共 26 条
[1]   (1R,3R)-2-METHYLENE-1,3-DITHIOLANE 1,3-DIOXIDE - A HIGHLY REACTIVE AND HIGHLY SELECTIVE CHIRAL KETENE EQUIVALENT [J].
AGGARWAL, VK ;
DRABOWICZ, J ;
GRAINGER, RS ;
GULTEKIN, Z ;
LIGHTOWLER, M ;
SPARGO, PL .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :4962-4963
[2]   Investigation of the effects of the structure and chelate size of bis-oxazoline ligands in the asymmetric copper-catalyzed cyclopropanation of olefins: Design of a new class of ligands [J].
Bedekar, AV ;
Koroleva, EB ;
Andersson, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2518-2526
[3]   DIENOPHILICITY OF CAPTODATIVE OLEFINS .7. DIELS-ADLER CYCLO-ADDITIONS OF ALPHA-METHYLTHIO METHYL ACRYLATE, THERMAL-REACTIONS, LEWIS ACID-CATALYZED REACTIONS AND TRANSFORMATIONS OF ADDUCTS [J].
BOUCHER, JL ;
STELLA, L .
TETRAHEDRON, 1988, 44 (12) :3607-3615
[4]   The application of the formyl C-H--O hydrogen bond postulate to the understanding of enantioselective reactions involving chiral boron Lewis acids and aldehydes [J].
Corey, EJ ;
Rohde, JJ .
TETRAHEDRON LETTERS, 1997, 38 (01) :37-40
[5]   The formyl C-H--O hydrogen bond as a critical factor in enantioselective reactions of aldehydes .4. Aldol, ethylation, hydrocyanation and Diels-Alder reactions catalyzed by chiral B, Ti and Al Lewis acids. [J].
Corey, EJ ;
BarnesSeeman, D ;
Lee, TW .
TETRAHEDRON LETTERS, 1997, 38 (25) :4351-4354
[6]   A conformational toolbox of oxazoline ligands. [J].
Davies, IW ;
Gerena, L ;
Cai, DW ;
Larsen, RD ;
Verhoeven, TR ;
Reider, PJ .
TETRAHEDRON LETTERS, 1997, 38 (07) :1145-1148
[7]   Application of indane-derived C-2-symmetric bis(oxazolines) in two-point binding asymmetric Diels-Alder reactions [J].
Davies, IW ;
Senanayake, CH ;
Larsen, RD ;
Verhoeven, TR ;
Reider, PJ .
TETRAHEDRON LETTERS, 1996, 37 (11) :1725-1726
[8]  
DAVIES LW, 1996, CHEM COMMUN, P1753
[9]   Chiral Lewis acid catalysts in Diels-Alder cycloadditions: Mechanistic aspects and synthetic applications of recent systems [J].
Dias, LC .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 1997, 8 (04) :289-332
[10]   SYNTHESIS OF ALPHA-PHENYLTHIO ENONES AND ESTERS OF ALPHA-PHENYLTHIO ALKENOIC ACIDS [J].
DURMAN, J ;
GRAYSON, JI ;
HUNT, PG ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1939-1945