Tetrahedron Letters p. 6227 - 6230 (1988)
Update date:2022-08-16
Topics:
Gribble, Gordon W.
Keavy, Daniel J.
Branz, Stephen E.
Kelly, William J.
Pals, Mark A.
The Diels-Alder reaction between 3-fluorobenzyne (1) and 2-alkylfurans (2) gives a mixture of syn adduct 3 and anti adduct 4.The syn cycloadduct invariably predominates and the regioselectivity increases in the order: R= Me< Et< i-Pr< t-Bu, to a maximum of 90percent syn adduct 3d for 2-tert-butylfuran.These results are rationalized in terms of a concerted nonsynchronous transition state that reflects an alkyl steric effect and a polarized aryne 1.
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