Use of β-Sulfonyl Vinyl Ketones as Equivalents to Vinyl Ketones in Robinson Annelation. Convergent, Highly Stereoselective Preparation of a Hydrindanol Related to Vitamin D from 2-Methylcyclopent-2-enone and Lithiated (E)-But-2-enyldiphenylphosphine Oxide

DOI: 10.1021/jo00282a038

Source and publish data:

Journal of Organic Chemistry p. 5162 - 5170 (1989)

Update date:2022-08-02

Topics:

Authors:

Haynes, Richard K.

Vonwiller, Simone C.

Hambley, Trevor W.

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Article abstract of DOI:10.1021/jo00282a038

Conjugate addition of lithiated (E)-but-2-enyldiphenylphosphine oxide (3) to 2-methylcyclopent-2-enone (2) in tetrahydrofuran at -20 deg C generates the enolate 8, which reacts rapidly with a series of β-sulfonyl vinyl ketones to generate unsaturated dike

Full text of DOI:10.1021/jo00282a038

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