Amine-Catalyzed Phospha-Michael Reaction of α,β-Unsaturated Aldehydes and Ketones with Multifunctional N‑Heterocyclic Phosphine-Thioureas as Phosphonylation Reagent

An efficient amine-catalyzed phospha-Michael addition reaction of α,β-unsaturated aldehydes/ketones with N-heterocyclic phosphines for the synthesis of γ-ketodiazaphosphonates has been developed. With freedom from nucleophile additives, this mild process affords a range of structurally diverse γ-ket...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 17; pp. 4372 - 4375
Main Authors Huang, Hai, Kang, Jun Yong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ACID-DERIVATIVES
DIETHYL PHOSPHITE
ALPHA-AMINO
ATOM ECONOMY
DIALKYL PHOSPHITES
CHALCONES
CHIRAL H-PHOSPHONATE
DIPHENYL PHOSPHITE
CONJUGATE ADDITION
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Summary:An efficient amine-catalyzed phospha-Michael addition reaction of α,β-unsaturated aldehydes/ketones with N-heterocyclic phosphines for the synthesis of γ-ketodiazaphosphonates has been developed. With freedom from nucleophile additives, this mild process affords a range of structurally diverse γ-ketodiazaphosphonates in moderate to excellent yields. Importantly, various α,β-unsaturated ketones were also tolerated in this process and gave moderate yields.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02121