An Intramolecular Nitroso-Meerwein–Ponndorf–Verley–Oppenauer Reaction to Access Fused Pyrrolidine Scaffolds

An Intramolecular Nitroso-Meerwein–Ponndorf–Verley–Oppenauer Reaction to Access Fused Pyrrolidine Scaffolds Full article

Journal

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

Output data

Year: 2024, Volume: 26, Number: 2, Pages: 450-455 Pages count : 6 DOI: 10.1021/acs.orglett.3c03552

Authors

Malykhin Roman S. ¹ , Aksenova Svetlana A. ^2,3 , Sukhorukov Alexey Yu. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova str. 28, Moscow 119991, Russian Federation
3	Moscow Institute of Physics and Technology (National Research University), Institutskiy per. 9, Dolgoprudny 141700, Moscow Region, Russian Federation

δ-Hydroxy chloronitroso compounds generated in situ from 1,2-oxazine N-oxides undergo a 1,5-hydride transfer related to the Meerwein–Ponndorf–Verley–Oppenauer reaction. Based on the process discovered, a three-step access to fused pyrrolidine scaffolds containing up to four contiguous stereogenic centers starting from simple nitrostyrenes and cycloalkenes or cyclodienes has been developed. The suggested reaction mechanism was confirmed by in situ UV–vis and ATR FT-IR monitoring and DFT calculations.

Malykhin R.S. , Aksenova S.A. , Sukhorukov A.Y.
An Intramolecular Nitroso-Meerwein–Ponndorf–Verley–Oppenauer Reaction to Access Fused Pyrrolidine Scaffolds
Organic Letters. 2024. V.26. N2. P.450-455. DOI: 10.1021/acs.orglett.3c03552 WOS Scopus OpenAlex

Web of science:	WOS:001146483300001
Scopus:	2-s2.0-85182578463
OpenAlex:	W4390660954

DB	Citing
OpenAlex	3
Scopus	3
Web of science	3