Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes-Reference-Cited by-同舟云学术

Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes

Published:2021 Issue:9 Volume:19 Page:1945-1949
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Cocco Andrea¹²³⁴⁵,Rubanu Maria Grazia¹²³⁴⁵,Sechi Maria Laura¹²³⁴⁵,Frongia Angelo¹²³⁴⁵^ORCID,Mastrorilli Pietro⁶⁷⁸⁹⁵,Degennaro Leonardo⁶⁷⁸⁹⁵,Colella Marco⁶⁷⁸⁹⁵,Luisi Renzo⁶⁷⁸⁹⁵^ORCID,Secci Francesco¹²³⁴⁵^ORCID

Affiliation:

1. Dipartimento di Scienze Chimiche e Geologiche

2. Università degli studi di Cagliari

3. Complesso Universitario di Monserrato

4. Monserrato

5. Italy

6. Dipartimento di Farmacia-Scienze del Farmaco

7. Università degli Studi di Bari

8. Aldo Moro

9. Bari I-70125

Abstract

Enantiomerically enriched oxaspiro- and azaspirohexanes were synthesized through a two-step addition of configurably stable Li-styrene oxide (or aziridine) to 3-substituted cyclobutanones and base-mediated Payne rearrangement sequence with high yields and selectivity.

Funder

Fondazione di Sardegna

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/OB/D0OB00771D

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3. Synthesis of unusually strained spiroheterocyclic ring systems and their exploits in synthesis