Highly Diastereoselective Esterification of Ketenes Generated In Situ from Acyl Chlorides with (R)??Pantolactone Derivatives

T Yamagami, M Hatsuda, M Utsugi…

Index: Yamagami, Takafumi; Hatsuda, Masanori; Utsugi, Masayuki; Kobayashi, Ryo; Moritani, Yasunori European Journal of Organic Chemistry, 2013 , # 33 p. 7467 - 7470

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Abstract

Abstract Our mechanistic investigations have revealed that Et 3 N is a key requirement for the highly diastereoselective formation of esters from the corresponding acyl chlorides with (R)-pantolactone via ketene-derived complexes. Furthermore, we have discovered that (R)- N-benzyl-pantolactam is a more effective chiral alcohol than (R)-pantolactone for the esterification of in situ generated ketenes.