Synthesis of Isoquinuclidines from Highly Substituted Dihydropyridines via the Diels-Alder Reaction

被引：45

作者：

Martin, Rhia M. ^{[1
]}

Bergman, Robert G. ^{[2
,3
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

[2] Univ Calif Berkeley, Lawrence Berkeley Natl Lab, Div Chem Sci, Berkeley, CA 94720 USA

[3] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 03期

关键词：

STEREOSELECTIVE-SYNTHESIS; HYDROISOQUINOLINE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; CHIRAL ISOQUINUCLIDINES; CYCLOADDITION REACTIONS; GROB FRAGMENTATION; MANNICH APPROACH; IBOGA ALKALOIDS; 1,2-DIHYDROPYRIDINE; DERIVATIVES;

D O I：

10.1021/ol303040r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereo- and regioselective Diels-Alder reaction for the synthesis of highly substituted isoquinuclidines from dihydropyridines and electron-deficient alkenes has been developed. While reactions with activated dienophiles proceed readily under thermal conditions, the use of Lewis acid additives is necessary to facilitate cycloadditions for less reactive alkenes. This procedure affords the target compounds in high yields and diastereoselectivities.

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页码：444 / 447

页数：4

相关论文

共 76 条

[51] STEREOSPECIFIC TOTAL SYNTHESES OF DECAHYDROQUINOLINE ALKALOIDS (+/-)-195A AND (+/-)-2-EPI-195A [J].

POLNIASZEK, RP ;

DILLARD, LW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4103-4110

[52] PREPARATION AND DIELS-ALDER REACTION OF N-CARBOMETHOXY-5-ETHYL-1,2-DIHYDROPYRIDINE - AN APPROACH FOR THE SYNTHESIS OF CATHARANTHINE [J].

RAUCHER, S ;

LAWRENCE, RF .

TETRAHEDRON LETTERS, 1983, 24 (29) :2927-2930

[53] TOTAL SYNTHESIS OF (+/-)-CATHARANTHINE [J].

RAUCHER, S ;

BRAY, BL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17) :3236-3237

[54]

Reding MT, 2002, HETEROCYCLES, V56, P313

[55]

Reine I, 2002, HETEROCYCL COMMUN, V8, P173

[56] Studies toward the synthesis of spirolucidine. Preparation of ABC and EF ring fragments [J].

Sahn, James J. ;

Bharathi, Pandi ;

Comins, Daniel L. .

TETRAHEDRON LETTERS, 2012, 53 (11) :1347-1350

[57] A Diels-Alder approach to the stereoselective synthesis of 2,3,5,6-tetra- and 2,3,4,5,6-pentasubstituted piperidines [J].

Sales, M ;

Charette, AB .

ORGANIC LETTERS, 2005, 7 (26) :5773-5776

[58] Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis [J].

Satoh, Tetsuya ;

Miura, Masahiro .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) :11212-11222

[59] Asymmetric synthesis of isoquinuclidines by Diels-Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst [J].

Seki, Chigusa ;

Hirama, Masafumi ;

Hutabarat, N. D. M. Romauli ;

Takada, Junko ;

Suttibut, Chonticha ;

Takahashi, Hideto ;

Takaguchi, Takuya ;

Kohari, Yoshihito ;

Nakano, Hiroto ;

Uwai, Koji ;

Takano, Nobuhiro ;

Yasui, Mitsukuni ;

Okuyama, Yuko ;

Takeshita, Mitsuhiro ;

Matsuyama, Haruo .

TETRAHEDRON, 2012, 68 (06) :1774-1781

[60] Direct transition metal-catalyzed functionalization of heteroaromatic compounds [J].

Seregin, Ilya V. ;

Gevorgyan, Vladimir .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1173-1193

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