Preparation of Optically Pure Tertiary Phosphine Oxides via the Addition of P‑Stereogenic Secondary Phosphine Oxide to Activated Alkenes

Functionalized P,C-stereogenic tertiary phosphine oxides were prepared by the addition of (R P)-menthyl phenylphosphine oxide to activated olefins, in high drP and drC, and were isolated in excellent yields. The reaction was readily catalyzed by Ca­(OH)2 or occurred with gentle heating. A wide range...

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Published inJournal of organic chemistry Vol. 81; no. 17; pp. 7644 - 7653
Main Authors Wang, Ji-Ping, Nie, Shao-Zhen, Zhou, Zhong-Yang, Ye, Jing-Jing, Wen, Jing-Hong, Zhao, Chang-Qiu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HYDROPHOSPHINATION
SUBSTITUTION
N-PHOSPHONYL IMINES
ENANTIOSELECTIVE SYNTHESIS
LIGANDS
CATALYZED ASYMMETRIC ALKYLATION
STEREOCHEMISTRY
PEPTIDE-SYNTHESIS
BORANES
CHROMATOGRAPHY
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Summary:Functionalized P,C-stereogenic tertiary phosphine oxides were prepared by the addition of (R P)-menthyl phenylphosphine oxide to activated olefins, in high drP and drC, and were isolated in excellent yields. The reaction was readily catalyzed by Ca­(OH)2 or occurred with gentle heating. A wide range of substrates, including vinyl ketones, esters, nitriles, and nitro alkenes, can be used in the reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.6b01371