Reversal of diastereoselection in the addition of Grignard reagents to chiral 2-pyridyl tert-butyl (Ellman) sulfinimines

Tetrahedron Letters

Volumn 45, Issue 35, 2004, Pages 6641-6643

  Kuduk, Scott D ^a   DiPardo, Robert M ^a   Chang, Ronald K ^a   Ng, Christina ^a   Bock, Mark G ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Chiral amines; Diastereoselection; tert Butyl sulfinamide

Indexed keywords

ALDEHYDE; AMINE; IMINE; REAGENT;

ADDITION REACTION; ARTICLE; CHELATION; CHEMICAL ANALYSIS; CHIRALITY; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; GRIGNARD REACTION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 4143071432     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.003     Document Type: Article

References (16)

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9. 3Al
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14. The reaction of lithium enolates with 3-pyridyl tert-butyl sulfinimines did not exhibit reversal of selectivity. See: T.P. Tang, and J.A. Ellman J. Org. Chem. 64 1999 12
15. 2leads to the reverse addition product (Ref. 12). The 2-pyridyl sulfinimines described herein are essentially unaffected by solvent effects
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