Enantioselective [2,3]-Wittig rearrangement of allyl picolyl ethers with chiral lithium amides
Year: 2025
Type: article
Abstract: Enantiomerically pure homoallylic alcohols containing pyridine substructure are useful as chiral ligands for asymmetric synthesis and as building blocks for the synthesis of biologically active chiral compounds and natural products. We have successfully performed the highly enantioselective [2,3]-Wittig rearrangement of 2-allyl picolyl ethers using chiral bidentate lithium amides to give 1-(2-pyridyl)-3-butenols with up to 95% ee, and demonstrated that the resulting chiral bidentate diamines, regenerated after the formation of lithioenamines, are excellent chiral ligands for the enantioselective [2,3]-Wittig rearrangement.
Source: RSC Advances
DOI: 10.1039/d5ra06385j
Authors: Midori Kawasaki, Kenji Yatsuzuka, Ryuichi Shirai
Institution: Doshisha Women's College of Liberal Arts
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $1,042
OpenAlex ID: W4414669957