Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives

Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2021, Volume: 23, Number: 13, Pages: 5266-5270 Pages count : 5 DOI: 10.1021/acs.orglett.1c01814

Authors

Milyutin Constantine V. ¹ , Komogortsev Andrey N. ¹ , Lichitsky Boris V. ¹ , Melekhina Valeriya G. ¹ , Minyaev Mikhail E. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow 119991, Russian Federation

We elaborate a novel one-step photochemical method for the synthesis of spiro-γ-butyrolactone derivatives from 3-hydroxypyran-4-ones. The suggested approach is based on a cascade process including initial photoinduced contraction of 4-pyranone ring followed by intramolecular cyclization leading to the final spiro system. A distinctive feature of the proposed method is intramolecular trapping of unstable α-hydroxydiketone intermediate formed in situ as a result of a photochemical reaction. The structures of two synthesized 1-oxaspiro[4.4]non-8-ene-2,6,7-triones were determined by X-ray diffraction.

Milyutin C.V. , Komogortsev A.N. , Lichitsky B.V. , Melekhina V.G. , Minyaev M.E.
Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives
Organic Letters. 2021. V.23. N13. P.5266-5270. DOI: 10.1021/acs.orglett.1c01814 WOS Scopus OpenAlex

Web of science:	WOS:000670661700064
Scopus:	2-s2.0-85110277191
OpenAlex:	W3176647465

DB	Citing
OpenAlex	19
Web of science	18
Scopus	17