Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones using thiourethane ligands

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1767-1770

  Bennett, Simon M W ^a   Brown, Stephen M ^b   Muxworthy, James P ^b   Woodward, Simon ^a  

^a UNIVERSITY OF HULL   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; ORGANOMETALLIC COMPOUND; URETHAN DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033605181     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02686-0     Document Type: Article

References (24)

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19. 5. The only >90% e.e. catalytic conjugate additions of this substrate class are rhodium-catalysed, see: Sakai, M; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579-5580. Enantioselective addition of alkyl groups is problematic and has not been described before
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21. p 113.4. Correct combustion analysis or HRMS in both cases.
22. 4 (15.7 mg, 0.05 mmol) and the mixture stirred (1 min, -20°C). Then at the desired temperature (-20°C) the organometallic (0.5 mL of 1.5 M solution, 0.75 mmol) and enone (0.5 mL of 1.0 M solution, 0.50 mmol) were introduced sequentially in a dropwise manner over 20 min. The reaction mixture was stirred for a further 20 min then quenched with HCl(aq.) and filtered (twice) through flash silica. Pentadecane (50 μL) was added and the chemical yield/e.e. obtained by GC using an oktakis-(6-O-methyl-2,3-di-O-pentyl)-γ-cyclodextrin column.
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