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Literature DB >> 19877599

Convergent synthesis of stereodefined exo-alkylidene-gamma-lactams from beta-halo allylic alcohols.

Shuhei Umemura¹, Martin McLaughlin, Glenn C Micalizio.

Abstract

A convergent process for the assembly of stereodefined mono- and bicyclic exo-alkylidene-gamma-lactams is described that proceeds through the union of beta-halo allylic alcohols, aromatic imines, and CO. Overall, regio- and stereoselective Ti-mediated reductive cross-coupling, followed by Pd-catalyzed carbonylation, can be performed in a one- or two-pot procedure, defining a highly selective three-component coupling process for heterocycle synthesis.

Entities: Chemical Gene

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Year: 2009 PMID： 19877599 PMCID： PMC2787655 DOI： 10.1021/ol9022134

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

14 in total

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6. Low-valent titanium-mediated stereoselective alkylation of allylic alcohols.

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8. Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

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9. An alkoxide-directed intermolecular [2+2+1] annulation: a three-component coupling reaction for the synthesis of tetrasubstituted alpha,beta-unsaturated gamma-lactams.

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10. Stereoselective cross-coupling between allylic alcohols and aldimines.

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4. Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions.

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5. Convergent and stereodivergent synthesis of complex 1-aza-7-oxabicyclo[2.2.1]heptanes.

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6. Metallacycle-Mediated Cross-Coupling with Substituted and Electronically Unactivated Alkenes.

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7. The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

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7 in total