Reactions of dibenzylphosphine oxide with α,β-unsaturated nitriles: Synthesis of aminophospholene oxides

Reactions of dibenzylphosphine oxide with α,β-unsaturated nitriles: Synthesis of aminophospholene oxides Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2002, Volume: 51, Number: 4, Pages: 671-677 Pages count : 7 DOI: 10.1023/A:1015876403665

Tags

α,β-unsaturated nitriles; Aminophospholene oxides; Dibenzylphosphine oxide; Heterocycles; Nucleophilic addition; Phosphorylation; Terpenoids

Authors

Kolesnik V.D. ¹ , Tkachev A.V. ²

Affiliations

1	(Scopus) Department of Natural Sciences, Novosibirsk State University, 2 ul. Pirogova, 630090 Novosibirsk, Russian Federation
2	(Scopus) N. N. Vorozhtsov Novosibirsk I., Siberian Branch, Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090 Novosibirsk, Russian Federation

The reactions of dibenzylphosphine oxide with α,β-unsaturated nitriles in the presence of two equivalents of NaH in ButOMe afforded substituted aminophospholene oxides in 20-83% yields. In the presence of bulky substituents at the α and γ positions of unsaturated nitriles, cyclization of the initially formed adducts proceeds with high stereoselectivity to give the single stereoisomer of aminophospholene oxide.

Kolesnik V.D. , Tkachev A.V.
Reactions of dibenzylphosphine oxide with α,β-unsaturated nitriles: Synthesis of aminophospholene oxides
Russian Chemical Bulletin. 2002. V.51. N4. P.671-677. DOI: 10.1023/A:1015876403665 WOS Scopus РИНЦ РИНЦ OpenAlex

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Scopus:	2-s2.0-0141721502
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OpenAlex:	W2949086464

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