Tetrahedron

Chiral induction in photochemical reactions: V. Regio-and diastereoselectivity in the photochemical [2+ 2] cycloaddition of chiral cyclenone-3-carboxylates with 1, 1'- …

H Herzog, H Koch, HD Scharf, AJ Runsink

Index: Herzog, Heinz; Koch, Hartmut; Scharf, Hans-Dieter; Runsink, Jan Tetrahedron, 1986 , vol. 42, # 13 p. 3547 - 3558

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Citation Number: 32

Abstract

The chiral cyclenone-3-carboxylates 5-12 induce high regio-but only fair diastereoselectivities in tne photochemical [2+ 2] cycloaddition with 1, 1'-diethoxyethene 23. Cyclohex-2-ene-1-one-3-carboxylates gain higher diastereoselectivites compared to the ringhomologous cyclopent-2-ene-1-one-3-carboxylates. The face-differentiating effect of the chiral 3-estergroup is not only sterically caused but also indicates an electronic ...