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Chiral cycloalkylidene α,β-unsaturated iminium approach to stereoselective formal [3+3] cycloaddition reaction in spiroheterocycle synthesis

✍ Scribed by Michael J McLaughlin; Hong C Shen; Richard P Hsung

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 115 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)02018-9

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✦ Synopsis

An approach to stereoselective formal [3+3] cycloaddition reaction using chiral cycloalkylidene a,b-unsaturated iminiums is described here leading to preparations of spiroheterocycles in modest stereoselectivity. The reversibility of 6p-electron electrocyclic ring closure did not always lead to the thermodynamically more favored product. These observations led to other useful mechanistic understanding of electrocyclic ring closure of 1-oxatrienes.

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