Acid-promoted retro-Mannich reaction of N-protected tropenones to 2-substituted pyrroles

被引：16

作者：

Cramer, N ^{[1
]}

Juretschke, J ^{[1
]}

Laschat, S ^{[1
]}

Baro, A ^{[1
]}

Frey, W ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 07期

关键词：

fragmentation; ketones; regioselectivity; Mannich reaction; tropenones;

D O I：

10.1002/ejoc.200300804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-protected tropenone 4 undergoes highly regioselective retro-Mannich reactions to 2-pyrrolyl ketones 5 and 7 in the presence of Lewis or Bronsted acids. Analogously, the pyrrole derivative 8a was obtained by using subsequent nucleophilic trapping with TMSCN. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

引用

页码：1397 / 1400

页数：4

共 28 条

[1] NEW ROUTES TO SUBSTITUTED TROPONES [J].

BARBOSA, LCA ;

MANN, J ;

WILDE, PD ;

FINCH, MW .

TETRAHEDRON, 1989, 45 (14) :4619-4626

[2]

BERKOWITZ SS, 1974, CURR THER RES CLIN E, V16, P442

[3] Radical aromatic substitution via atom-transfer addition [J].

Byers, JH ;

Campbell, JE ;

Knapp, FH ;

Thissell, JG .

TETRAHEDRON LETTERS, 1999, 40 (14) :2677-2680

[4] Enzymatic resolution of tropinone derivatives [J].

Cramer, N ;

Laschat, S ;

Baro, A .

SYNLETT, 2003, (14) :2178-2181

[5] GENERATION AND [4 + 3] CYCLO-ADDITION OF CYCLOPENTENYLIUM-2-OLATE FROM 2-CHLOROCYCLOPENTANONE UNDER ALCOHOLYSIS CONDITIONS [J].

FOHLISCH, B ;

JOACHIMI, R .

CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (12) :1951-1960

[6]

FUJI M, 1992, CHEM PHARM BULL, V40, P2344

[7] MECHANISMS AND STEREOCHEMISTRY OF HETEROLYTIC FRAGMENTATION [J].

GROB, CA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :535-&

[8] HETEROLYTIC FRAGMENTATION . A CLASS OF ORGANIC REACTIONS [J].

GROB, CA ;

SCHIESS, PW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (01) :1-&

[9] N-P-TOLUENESULFONYLPYRROLES FROM 1,3-DIENES [J].

HARRINGTON, PJ ;

SANCHEZ, IH .

SYNTHETIC COMMUNICATIONS, 1994, 24 (02) :175-180

[10]

HOPKINS PB, 1996, ADV DNA SEQ, V2, P217

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