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Synthesis and Diels ‐ Alder Reactivity of 1‐(Dimethoxy)methyl‐2,3,5,6‐tetramethylidene‐7‐oxabicyclo[2.2.1]heptane . Preliminary communication
Author(s) -
Métral JeanLuc,
Vogel Pierre
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680207
Subject(s) - chemistry , stereoselectivity , acetal , reagent , tandem , heptane , diels–alder reaction , reactivity (psychology) , stereochemistry , organic chemistry , catalysis , medicine , materials science , alternative medicine , pathology , composite material
A short synthesis of the title compound 13 is reported. The acetal group in 13 enables one to control the regio‐ and stereoselectivity of the two successive Diels ‐ Alder additions of the tetraene. The first addition is significantly faster than the second one, thus making 13 a versatile reagent for regio‐ and stereoselective ‘tandem’ cycloadditions.