Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

New chiral regioisomeric γ-hydroxyphosphine ligands were synthesized from α-pinene. The key transformation was the thermal [2,3]-sigmatropic rearrangement of allyldiphenylphosphinites, obtained from (1 R ,2 R ,4 S ,5 R )-3-methyleneneoisoverbanol and (1 R ,2 R ,3 R ,5 R )-4-methyleneneoisopinocamphe...

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Bibliographic Details
Published in:	Beilstein journal of organic chemistry Vol. 15; no. 1; pp. 2493 - 2499
Main Authors:	Kmieciak, Anna, Krzemiński, Marek P
Format:	Journal Article
Language:	English
Published:	Frankfurt am Main Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 22-10-2019 Beilstein-Institut
Subjects:	[2,3]-sigmatropic rearrangement Alcohol Aqueous solutions Chemistry Chromatography Full Research Paper Hydrogen Hydrogenation isopinocamphone Ligands monoterpenes Oxidation Oxides Phosphine phosphines Sodium verbanone α-Pinene
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Summary:	New chiral regioisomeric γ-hydroxyphosphine ligands were synthesized from α-pinene. The key transformation was the thermal [2,3]-sigmatropic rearrangement of allyldiphenylphosphinites, obtained from (1 R ,2 R ,4 S ,5 R )-3-methyleneneoisoverbanol and (1 R ,2 R ,3 R ,5 R )-4-methyleneneoisopinocampheol, to allylphosphine oxides. Hydroxy groups were introduced stereoselectively through a hydroboration–oxidation reaction proceeding from the less hindered site providing a trans relationship between the hydroxy and the phosphine substituents.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1860-5397 2195-951X 1860-5397
DOI:	10.3762/bjoc.15.242