Convergent synthesis of stereodefined exo-alkylidene-γ-lactams from β-halo allylic alcohols

Organic Letters

Volumn 11, Issue 23, 2009, Pages 5402-5405

  Umemura, Shuhel ^a   McLaughlin, Martin ^a   Micalizio, Glenn C ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; IMINE; LACTAM; PALLADIUM; PROPANOL;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; IMINES; LACTAMS; MOLECULAR STRUCTURE; PALLADIUM; PROPANOLS; STEREOISOMERISM;

EID: 72449190565     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9022134     Document Type: Article

References (27)

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25. 4, and concentrated in vacuo. The crude material was purified by column chromatography on silica gel (1/40-1/30 EtOAc/Hexanes) to yield haloallylic amine 17 as a colorless oil (811 mg, 67%, dr ≥ 20:1).
26. 3N (114 μL, 83 mg, 0.820 mmol). The reaction was placed under an atmosphere of CO by briefly exposing the reaction vessel to vacuum and backfilling with carbon monoxide from a balloon. The atmosphere of CO was maintained by a balloon for the remainder of the reaction. The reaction vessel was then submerged in a preheated oil bath (70 °C) and stirred for 12 h. The reaction mixture was then allowed to cool to ambient temperature, diluted with EtOAc, filtered through cotton, and concentrated in vacuo. The crude material was purified by column chromatography on silica gel (1/10-→1/5 EtOAc/Hexanes) to yield γ-lactam 18 as a white solid (111 mg, 87%).
27. 4 and concentrated in vacuo. The crude material was purified by column chromatography on silica gel (1/10→1/5 EtOAc/Hexanes) to yield y-lactam 18 as a white solid (89 mg, 73%, dr ≥ 20:1).