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Volumn , Issue 5, 2008, Pages 777-781

Gold-catalyzed [2+2] cyclization of alkyne-propargylic pivaloates to fused bicyclic compounds

Author keywords

Bicyclic compounds; Catalyst; Cyclization; Gold; Pivaloate

Indexed keywords

ALKYNE; BICYCLO COMPOUND; GOLD;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; HYDROGENATION;

EID: 41449103020 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032110 Document Type: Article

Times cited : (3)

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- Typical Experimental Procedure for Cyclization of 4a to 7a In a 5 mL new test tube were placed AuCl(PPh3, 7.0 mg, 14.0 μmol, 5 mol, and AgSbF6 (4.8 mg, 14 μmol) and added dried DCE (1.0 mL) under argon atmosphere. After being stirred for 10 min at 0°C, a DCE solution (0.5 mL) of diyne-propargylic pivaloate 4a (101.0 mg, 0.28 mmol) was added. The resulting mixture was stirred for 15 h at r.t. and the reaction was periodically monitored by TLC Upon completion, the solvent was removed under vacuum and the crude product was subjected to flash column chromatography (SiO2, n-hexane-EtOAc, 30:1) to afford the pure product 7a as a colorless oil. All new compounds were fully characterized by 1H NMR, 13C NMR, IR, and HRMS (ESMS, Compound 7a: IR (NaCl, 3301, 3064, 2940, 2869, 1707, 1671, 1491, 1287 cm-1. 1H NMR (400 MHz, CDCl3, δ, 8.07-8.04 m, 2 H, 7
- -1.

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