Alkylation and cyclopentannulation of phospholene derivatives |
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Authors: | Zbigniew Pakulski K Micha? Pietrusiewicz |
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Institution: | a Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland b Department of Organic Chemistry, Maria Curie-Sk?odowska University, Gliniana 33, 20-614 Lublin, Poland |
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Abstract: | The deprotonation of 1-phenyl-3-phospholene 1-oxide, 1-sulfide or 1-borane with 1 or 2 equiv of LDA, followed by quenching with electrophiles gave a range of 2-mono- or 2,5-disubstituted phospholene derivatives in good yield. Only trans substitution in relation to the P-Ph group was observed. Treatment of lithiated phospholene intermediates with 1,3-dihaloalkanes afforded annulated 2-phenyl-2-phosphabicyclo3.3.0]oct-3-ene derivatives. The annulation reactions occurred with high regio- and stereoselectivity and led to the exclusive formation of the exo-Ph-P substituted products. |
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Keywords: | Phospholene Alkylation Cyclopentannulation |
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