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 2019-10, Vol.15 (1), p.2493-2499
Main Authors: Kmieciak, Anna, Krzemiński, Marek P
Format: Article
Language:English
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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.15.242