Highly stereoselective addition of organometallic reagents to N-tert-butanesulfinyl imines derived from 3- and 4-substituted cyclohexanones

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1645-1647

  McMahon, Jeffrey P ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTANE; CYCLOHEXANONE DERIVATIVE; IMINE; N TERT BUTANESULFINYLIMINE DERIVATIVE; ORGANOMETALLIC COMPOUND; REAGENT; SULFINAMIDE; TERT BUTANESULFINAMIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; RACEMIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 2542615408     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0495220     Document Type: Article

References (11)

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9. Similar rationale is used to explain the selectivity of organometallic additions to cyclic ketones; see: Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry; Kluwer Academic: New York, 2001; Part B, p 457.
10. Although the individual imine isomers cannot be isolated, they can be observed on the NMR time scale.
11. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon Press: New York, 2002; pp 2-5.