Diastereoselective additions of nucleophiles to α-acetoxy ethers using the α-(trimethylsilyl)benzyl auxiliary

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2367-2370

  Rychnovsky, Scott D ^a   Cossrow, Jennifer ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CARBENOID; ETHER DERIVATIVE; SILANE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; DIASTEREOISOMER; GAS CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 0141741529     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0347904     Document Type: Article

References (24)

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17. Configuration of adducts 7-9 were assigned by analogy to the allyltrimethylsilane addition and to the configuration of adduct 18.
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24. 1H NMR analysis of purified products. The minor diastereomer may be an artifact of the optical purity of α-acetoxy ether 17 (88% ee at TBS-protected alcohol, 98% ee at the α-TMS benzyloxy position) and silyl enol ether 15 (91% ee). These optical purities would lead to a diastereomeric mixture containing ca. 90% 18 with perfect selectivity in the coupling reaction. For proof of the stereochemistry, see Supporting Information.