Hydroxy group directivity in the epoxidation of chiral allylic alcohols: Control of diastereoselectivity through allylic strain and hydrogen bonding

Accounts of Chemical Research

Volumn 32, Issue 8, 1999, Pages 703-710

  Adam, Waldemar ^a   Wirth, Thomas ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; HYDROXYL GROUP;

CATALYST; CHEMICAL STRUCTURE; EPOXIDATION; HYDROGEN BOND; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032822880     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9800845     Document Type: Review

References (45)

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44. A reviewer has pointed out that hydrogen bonding between the allylic hydroxy group and the peracid may be more significant than allylic strain in controlling the π-facial selectivity. Clarification of this point requires high-level calculations on our stereochemical probe, the chiral allylic alcohol 4c. All we claim is that the hydroxy group directivity is a cooperative effect between hydrogen bonding and conformational alignment.
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