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Organic Letters

Volumn 11, Issue 3, 2009, Pages 705-708

PQS: A new platform for micellar catalysis. RCM reactions in water, with catalyst recycling

(2) Lipshutz, Bruce H a Ghorai, Subir a

a UNIVERSITY OF CALIFORNIA (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 62149140098 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol8027829 Document Type: Article

Times cited : (86)

References (40)

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- Determined by dynamic light scattering measurements using a Brookhaven Laser Light Scattering instrument.

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- Determined at Augustine Scientific, Newbury, Ohio by surface tension measurements using the Wilhelmy Plate Method on a Kruss K100 Tensiometer.

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40
- 62149139434
- Representative Procedure, Figure 2, compound 11) Precursor diene (24 mg, 0.10 mmol) and catalyst 2 (7.5 mg, 0.002 mmol) were both added into a Biotage 2-5 mL microwave reactor vial with a Teflon-coated stir bar at room temperature and sealed with a septum. H2O (1.0 mL; all RCM reaction were conducted at 0.1 M unless stated otherwise) was added via syringe, and the resulting solution was allowed to stir at room temperature for 3 h. The homogeneous reaction mixture was then diluted with EtOAc (5 mL) and filtered through a bed of silica gel layered over Celite, and the bed was further washed (2 × 10 mL) with EtOAc to collect all of the cyclized material. The volatiles were removed in vacuo to afford the crude product, which was subsequently purified by flash chromatography using silica gel (4% EtOAc/hexanes) to afford the compound as a colorless liquid (19 mg, 92, IR neat, 3085, 3001, 2940, 2840, 1598, 1463, 1428, 1349, 1295, 1242, 1204, 1155, 1054, 102
- + = 206.0943, found 206.0952.

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