Stereoselectivity of Michael Addition of P(X)-H-Type Nucleophiles to Cyclohexen-1-ylphosphine Oxide: The Case of Base-Selective Transformation

The Journal of Organic Chemistry
Magdalena JaklińskaMarek Stankevič

Abstract

Michael addition of phosphorus nucleophiles to the unsymmetrically substituted tert-butyl(1,4-cyclohexadien-3-yl)phosphine oxide and its derivatives has been described. The addition proceeds with the formation of the mixture of two isomeric products with good yield and diastereoselectivity. The reaction of tert-butyl(cyclohexen-1-yl)methylphosphine oxide with phosphorus nucleophiles is base sensitive and might afford two epimers which differ at one chirality center. The absolute configuration of the products has been assigned on the basis of conformational and (1)H NMR analysis, and the mechanism of the reaction has been discussed. The Michael addition of phosphorus nucleophiles is postulated to proceed with or without consecutive epimerization of two α-carbanions.

References

Sep 9, 2005·Organic Letters·Carl A BusaccaChris H Senanayake
Jan 17, 2008·The Journal of Organic Chemistry·Carl A BusaccaChris H Senanayake
Mar 8, 2008·Organic Letters·Darren SteadAdam Sanderson
Apr 9, 2008·Organic Letters·Sanzhong LuoJin-Pei Cheng
Mar 8, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Christine J CooperDavid R Allan
Feb 2, 2012·The Journal of Organic Chemistry·Marek StankevičK Michał Pietrusiewicz
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Sep 17, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·M AlagesanN Dharmaraj

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Citations

Nov 16, 2019·Beilstein Journal of Organic Chemistry·Anna Kmieciak, Marek P Krzemiński

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