Diastereo- and Enantioselective Synthesis of Pyrrolo[1,4]benzodiazepines through Decarboxylative Photocyclization

Axel G Griesbeck; Wolfgang Kramer; Johann Lex

doi:10.1002/1521-3773(20010202)40:3<577::AID-ANIE577>3.0.CO;2-L

Diastereo- and Enantioselective Synthesis of Pyrrolo[1,4]benzodiazepines through Decarboxylative Photocyclization

Angew Chem Int Ed Engl. 2001 Feb 2;40(3):577-579. doi: 10.1002/1521-3773(20010202)40:3<577::AID-ANIE577>3.0.CO;2-L.

Authors

Axel G Griesbeck¹, Wolfgang Kramer¹, Johann Lex¹

Affiliation

¹ Institut für Organische Chemie Universität Köln Greinstrasse 4, 50939 Köln, Germany, Fax: (+49) 221-470-5057.

PMID: 29712029
DOI: 10.1002/1521-3773(20010202)40:3<577::AID-ANIE577>3.0.CO;2-L

Abstract

Memory of chirality in triplet 1,7-diradicals was detected for the first time and to a remarkably high degree in the decarboxylative photocyclization of the proline derivative of N-phthaloyl anthranilic acid 1 into 2 (X=H: 45 % yield, 86 % ee; X=Cl: 50 % yield, 79 % ee).

Keywords: atropisomerism; circular dichroism; diradicals; memory of chirality; photochemistry.