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ChemInform Abstract: Trifluoromethanesulfonic Acid, an Efficient Catalyst for the Hetero Diels-Alder Reaction and an Improved Synthesis of Mefrosol.

✍ Scribed by V. K. AGGARWAL; G. P. VENNALL; P. N. DAVEY; C. NEWMAN

Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Trifluoromethanesulfonic Acid, an Efficient Catalyst for the Hetero Diels-Alder Reaction and an Improved Synthesis of Mefrosol.

-The hetero Diels-Alder reaction between unactivated dienes with alkyl groups in the 2-position (cf. isoprene (II)) and aromatic aldehydes is effectively promoted by catalytic triflic acid providing pyrans. However, the dienes (IX) give the Prins reaction under similar conditions affording 1,3-dioxoles. Hydrogenation of adduct (IIIa) completes the short and economic synthesis of the fragrance material mefrosol (IV). -(

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