Stabilized Sulfur Ylides as Synthetic Equivalents of the Carbyne Anion: A Domino-Type Double Annulation Approach to Indane-Fused Isoxazoline N -Oxides

Stabilized Sulfur Ylides as Synthetic Equivalents of the Carbyne Anion: A Domino-Type Double Annulation Approach to Indane-Fused Isoxazoline N -Oxides Full article

Journal

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

Output data

Year: 2025, Volume: 27, Number: 45, Pages: 12687-12692 Pages count : 6 DOI: 10.1021/acs.orglett.5c04140

Authors

Okladnikov Ilya V. ¹ , Malykhin Roman S. ¹ , Lesnikov Vladislav K. ¹ , Sukhorukov Alexey Yu. ¹

Affiliations

1	Laboratory of Organic and Metal−Organic Nitrogen−Oxygen Systems (LOMONOS), N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russian Federation

The reaction of electron-withdrawing group (EWG)-stabilized sulfur ylides with ortho-formyl-substituted nitrostyrenes affords indane-fused isoxazoline N-oxides as a result of a double annulation process. In this reaction, the ylide acts as a synthetic equivalent of the carbyne anion to form three new bonds and a quaternary stereogenic center. The developed double annulation reaction is applicable to various types of stabilized sulfur ylides and is tolerant to sensitive functional groups. Post-transformations of the resulting fused isoxazoline N-oxides produce useful polyfunctionalized indane derivatives bearing several contiguous stereogenic centers.

Okladnikov I.V. , Malykhin R.S. , Lesnikov V.K. , Sukhorukov A.Y.
Stabilized Sulfur Ylides as Synthetic Equivalents of the Carbyne Anion: A Domino-Type Double Annulation Approach to Indane-Fused Isoxazoline N -Oxides
Organic Letters. 2025. V.27. N45. P.12687-12692. DOI: 10.1021/acs.orglett.5c04140 WOS Scopus OpenAlex

Web of science:	WOS:001604987300001
Scopus:	2-s2.0-105021864929
OpenAlex:	W4415711134

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