Stereoselective Diels-Alder reactions of chiral anthracenes

被引:46
作者
Sanyal, A [1 ]
Snyder, JK [1 ]
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
关键词
D O I
10.1021/ol006206m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Various chiral (9-anthryl)carbinol templates undergo Diels-Alder cycloadditions with a variety of symmetric and nonsymmetric dienophiles with excellent pi-facial selectivity and regioselectivity, under both thermal and Lewis acid catalyzed conditions.
引用
收藏
页码:2527 / 2530
页数:4
相关论文
共 30 条
[1]   Enantiopure building blocks for marine natural products via differentiation of enantiotopic groups [J].
Beil, W ;
Jones, PG ;
Nerenz, F ;
Winterfeldt, E .
TETRAHEDRON, 1998, 54 (26) :7273-7292
[2]   STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES [J].
BLOCH, R ;
GUIBEJAMPEL, E ;
GIRARD, C .
TETRAHEDRON LETTERS, 1985, 26 (34) :4087-4090
[3]   SYNTHESIS OF BOTH ENANTIOMERS OF GAMMA-SUBSTITUTED ALPHA, BETA-UNSATURATED GAMMA-LACTONES [J].
BLOCH, R ;
GILBERT, L .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4603-4605
[4]   Use of 9-anthrylcarbinol derivatives as chiral auxiliaries .2. Asymmetric 1,3-dipolar cycloaddition [J].
Carriere, A ;
Virgili, A ;
Figueredo, M .
TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2793-2796
[5]   Complete diastereofacial selective cycloaddition of new sulfinyl dienophiles (Ss)-and (Rs)-(-)menthyl alpha-(2-methoxyphenylsulfoxyl)acylate with anthracene under chelation control [J].
Chau, TY ;
Lin, HC ;
Hu, WH .
SYNTHETIC COMMUNICATIONS, 1996, 26 (10) :1867-1874
[6]   STRUCTURAL EFFECTS CONTROLLING THE RATE OF THE RETRO-DIELS-ALDER REACTION IN ANTHRACENE CYCLOADDUCTS [J].
CHUNG, YS ;
DUERR, BF ;
MCKELVEY, TA ;
NANJAPPAN, P ;
CZARNIK, AW .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1018-1032
[7]   A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].
COREY, EJ ;
BAKSHI, RK .
TETRAHEDRON LETTERS, 1990, 31 (05) :611-614
[8]   THE FACE SELECTIVITY DIRECTED BY AN ALLYLIC GROUP OF A DIENE IN THE DIELS-ALDER REACTION IS REVERSED FROM THAT OF A DIENOPHILE [J].
FRANCK, RW ;
ARGADE, S ;
SUBRAMANIAM, CS ;
FRECHET, DM .
TETRAHEDRON LETTERS, 1985, 26 (27) :3187-3190
[9]  
GERSTENBERGER I, 1939, EUR J ORG CHEM, V4, P643
[10]   Stereoselective Diels-Alder reactions of hexachlorocyclopentadiene with chiral alkenes: New insights into the ''inside-alkoxy'' model of stereoselectivity [J].
Haller, J ;
Niwayama, S ;
Duh, HY ;
Houk, KN .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5728-5731