Palladium (II)-catalyzed asymmetric acetalization of alkenes

T Hosokawa, T Yamanaka, M Itotani…

Index: Hosokawa, Takahiro; Yamanaka, Toshio; Itotani, Motohiro; Murahashi, Shun-Ichi Journal of Organic Chemistry, 1995 , vol. 60, # 19 p. 6159 - 6167

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Citation Number: 46

Abstract

The terminal olefinic carbon of N-methacryloyl-2-oxazolidinones is smoothly acetalized by alcohols in the presence of PdClz catalyst. The use of 4 (S)-isopropyl-, phenyl-, and tert-butyl- 2-oxazolidinones as the chiral auxiliary resulted in the formation of the corresponding (2'SI- acetals in 61, 80, and 95% de, respectively. Reductive removal of the auxiliary with LiAIH4 followed by deacetalization produced (R)-3-hydroxy-2-methylpropanal. The enantiomer of ...