Tetrahedron Letters p. 4841 - 4844 (1996)
Update date:2022-08-29
Topics:
Myers, Andrew G.
Zheng, Bin
The Mitsunobu reaction of allylic alcohols with o- nitrobenzenesulfonylhydrazine (NBSH) as nucleophile proceeds at -30 °C with invertive displacement; warming the resultant N-allylic sulfonylhydrazine derivative to 23 °C then leads to allylic diazene formation followed by sigmatropic elimination of dinitrogen. This one-step method for reductive 1,3-transposition is shown to be efficient and highly regio- and stereocontrolled within a wide range of allylic alcohol substrates.
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