Reaction of. alpha.-(phenylsulfinyl) acetonitrile with aldehydes and ketones to. gamma.-hydroxyalkenenitriles and syntheses of terpenoids

T Ono, T Tamaoka, Y Yuasa, T Matsuda…

Index: Ono,T.; Tamaoka,T.; Yuasa,Y. Journal of the American Chemical Society, 1984 , vol. 106, p. 7890

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Citation Number: 38

Abstract

Abstract: Reaction of a-(phenylsulfiny1) acetonitrile (1) with aldehydes or ketones in the presence of base directly affords y-hydroxyalkenenitriles. Some terpenoids, such as dendrolasin (9), sirenin (17), and conjugated trienoic acid (3, 7, 11, 15-tetramethylhexadeca- 2, 4, 6, 10, 14-pentenoic acid (24)), were synthesized by employing the new C2 unit homologation method.

107-14-2

2-chloroacetonitrile

~95%

~9%

~77%

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