Organic Letters p. 509 - 511 (2008)
Update date:2022-07-29
Topics:
Bender, David M.
Peterson, Jeffrey A.
McCarthy, James R.
Gunaydin, Hakan
Takano, Yu
Houk
Esters of cyclopropanecarboxylic acid demonstrate a substantial increase in stability under both acid- and base-catalyzed hydrolytic conditions. Comparison of the stability of valacyclovir 13 with the cyclopropane analogue 14 shows that at 40 °C and pH 6 the half-life of 14 is >300 h while the value for 13 is 69.7 h. CBS-QB3 calculations on isodesmic reactions for transfer of groups from an alkane to an ester show that a cyclopropyl group provides hyperconjugative stabilization.
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