( S )‐1,1‐Diphenylprolinol Trimethylsilyl Ether

Abstract

( S )‐1,1‐Diphenylprolinol trimethylsilyl ether is readily prepared by the silylation of ( S )‐1,1 diphenylprolinol. Commercial sources of diphenylprolinol can be expensive, and current methods for the synthesis of diphenylprolinol and its derivatives are low yielding, practically challenging on scale, or include hazardous reagents such as phosgene. The method reported provides access to diphenylprolinol in two steps from the Boc‐protected methyl ester of proline, and the trimethylsilylether of diphenylprolinol via a single transformation from diphenyl prolinol.

Asymmetric Organocatalysis Enables Rapid Assembly of Portimine Precursor Chains

“…Stirring a mixture of 2-trimethylsiloxyfuran with commercial crotonaldehyde in the presence of 20 mol % d -proline-derived catalyst A gave, after hydrogenation of the crude mixture over Pd­(OH) 2 /C, butyrolactone 4 (Scheme ). Under optimized conditions, “ syn ” diastereomer (+)- 4 was isolated in good yield and selectivity in 20 g batches.…”