Practical Asymmetric Diels-Alder Additions to Camphor-10-sulfonic-Acid-Derived Acrylates

DOI: 10.1002/hlca.19830660747

Source and publish data:

Helvetica Chimica Acta p. 2358 - 2361 (1983)

Update date:2022-08-02

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Authors:

Oppolzer, Wolfgang

Chapuis, Christian

Kelly, Martha J.

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Article abstract of DOI:10.1002/hlca.19830660747

Starting from (+)-camphor-10-sulfonic acid (1) the chiral crystalline alcohols 3 and 11 were prepared in two steps.Lewis-acid-mediated <4+2>-additions of their acrylates to 1,3-dienes were studied.Notably, the crystalline acrylate 4 underwent TiCl2(OiPr)2-promoted Diels-Alder addition to cyclopentaniene giving after recrystallization efficiently the pure (2R)-adduct 5.

Full text of DOI:10.1002/hlca.19830660747

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