Asymmetric 1,4-reductions of hindered β-substituted cycloalkenones using catalytic SEGPHOS-ligated CuH

Organic Letters

Volumn 6, Issue 8, 2004, Pages 1273-1275

  Lipshutz, Bruce H ^a   Servesko, Jeff M ^a   Petersen, Tue B ^a   Papa, Patrick P ^a   Lover, Andrew A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; COPPER DERIVATIVE; KETONE DERIVATIVE; LIGAND; REAGENT;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CONJUGATION; HYDROSILYLATION; REDUCTION;

ANTINEOPLASTIC AGENTS; CATALYSIS; COPPER; CYCLOHEXANONES; KETONES; LIGANDS; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 2542502428     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0400185     Document Type: Article

References (17)

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14. Use of ligand 2 required 96 h to obtain an ee of 97%, whereas ligand 1 led to 5 at -35°C in 99.5% ee after 16 h.
15. Using ligand 1, absolute stereochemistry was confirmed by comparisons of rotation data with known products. 3 (R): comparison with commercial material. 4: (R) (Allinger, N. L.; Riew, C. K. J. Org. Chem. 1975, 40, 1316). 6: (R). 7: (S). 8: (S) (cf. ref 8).
16. 4, filtered, and concentrated by rotary evaporation with caution due to slight volatility. The residue was purified by fractional distillation to afford 58.14 g (88.5%) of the title compound. Analysis by chiral GC (Chiraldex B-DM 75) indicated an ee of 98.5%.
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