Substrate-directed divergent annulations of sulfur ylides: synthesis of functionalized bispirocyclopentane and bispirocyclopropane derivatives.
Org Biomol Chem
; 22(11): 2197-2202, 2024 Mar 13.
Article
em En
| MEDLINE
| ID: mdl-38411569
ABSTRACT
Herein, an efficient, substrate-directed divergent [2 + 3]/[2 + 1] annulation of tetra-substituted oxa-dienes and allylic sulfur ylides has been successfully developed. Under precise annulation regulation, a series of functionalized bispirocyclopentane and bispirocyclopropane derivatives were synthesized in a highly stereoselective and economical manner (up to 95% yield, >20 1 dr or >20 1 E/Z). This protocol offers the advantages of mild conditions, high chemo-, regio- and diastereoselectivity and broad substrate compatibility. In addition, the synthetic practicality of this protocol was evaluated through a scale-up preparation and a series of three-component reactions utilizing in situ generated sulfur ylides.
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MEDLINE
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En
Ano de publicação:
2024
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Article