Journal of Organic Chemistry p. 743 - 747 (1989)
Update date:2022-09-26
Topics:
Koerwitz, Frederick L.
Hammond, Gerald B.
Wiemer, David F.
To develop a new synthesis of vinyl silanes, a representative set of vinyl silane phosphates (VSP's) has been treated with several organocuprate reagents.With acyclic VSP's, phosphate substitution proceeds in generally good yields, giving a single stereoisomer of the vinyl silane with retention of the VSP stereochemistry.In the cyclic systems examined, yields are generally somewhat lower under the same reactions conditions.However, this new sequence offers a regiochemistry complementary to other syntheses of cyclic vinyl silanes, and an approach to higly substituted vinyl silanes applicable to both cyclic and acyclic systems.
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