Abstract
Reductive coupling of a,?-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, a-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids
Original language | English |
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Pages (from-to) | 3659 - 3664 |
Number of pages | 6 |
Journal | The Journal of Organic Chemistry |
Volume | 79 |
Issue number | 8 |
DOIs | |
Publication status | Published - 2014 |