Citation: Xue Shi MAO, A. A. VOLKERS, A. J. H. KLUNDER, Binne ZWANENBURG. Facial Selectivity in the Nucleophilic Additions of endo-Tricyclo [5.2.1.O^2.6]deca-2 (6),8-dien-3-one[J]. Chinese Chemical Letters, ;2001, 12(7): 581-584. shu

Facial Selectivity in the Nucleophilic Additions of endo-Tricyclo [5.2.1.O^2.6]deca-2 (6),8-dien-3-one

1.
Department of Organic Chemistry, NSR Center for Molecular Structure, Design and Synthesis, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands

Received Date: 26 April 2001

Fund Project: Mao is grateful to NSR center, University of Nijmegen for a postdoctoral fellowship.

Nucleophilic additions to endo-tricyclo [5.2.1.0^2.6]deca-2(6),8-dien-3-one 4 are described.Experimental results show high preference for exo-facial attack to the enone moiety of tricyclodecadienone. Steric hindrance is the main kinetically controlling factor in the nucleophilic reaction. The shielding effect and the stabilizing effect of the norbornene double bond favor the exo-facial attack also.
- Stereochemistry,
- nucleophilic addition.
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