Synthesis and  Diels ‐ Alder  Reactivity of 1‐(Dimethoxy)methyl‐2,3,5,6‐tetramethylidene‐7‐oxabicyclo[2.2.1]heptane . Preliminary communication | Zendy

Métral JeanLuc | Zendy; Vogel Pierre | Zendy

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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.

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