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31.41.3.1.1.2.4 Conjugate Addition to Activated Alkenes

DOI: 10.1055/sos-SD-131-00192

Demchuk, O. M.; Stankevič, M.; Pietrusiewicz, K. M.Science of Synthesis Knowledge Updates, (20151309.

Conjugate addition of phosphorus nucleophiles to activated alkenes, sometimes named as the phospha-Michael addition, represents one of the most versatile and powerful tools for the formation of P—C bonds.[‌136‌] Additions involving secondary phosphine oxides as nucleophiles are typically carried out under basic conditions using either a basic catalyst such as potassium carbonate,[‌137‌,‌138‌] alkaline alkoxides,[‌139‌] or 1,8-diazabicyclo[5.4.0]undec-7-ene,[‌140‌] or stronger bases (e.g., NaH, BuLi) in stoichiometric amounts.[‌141‌,‌142‌]

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Me8 M8 Meeeeeee Meeeeee Meeeee (%) ee 88 Mee
8-MeMM8M8 Me MMM eeeeeee 88 [‌888‌]
Me Me8MM8 eeeeeee 88 [‌888‌]
8,8,8-(MeM)8M8M8 Me Me(MMe)8 MMM 88 [‌888‌]
Me Me8MM8 eeeeeee 88 [‌888‌]

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Meeeeeeeeee 88

M8 M8 M8 M8 ee (%) Meeee (%) Mee
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Me Me Me Me 88 88 [‌888‌]
8-M8MM8M8 Me Me Me 88 88 [‌888‌]
Me 8-MeMM8M8 Me Me 88 88 [‌888‌]
Me 8-MeM8M8 Me Me 88 88 [‌888‌]

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8,8-Meeeee-8-(eeeeeeeeeeeeeeeeee)eeeeee-8-eeee 88; Meeeeee Meeeeeeee:[‌888‌]

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References


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