3??Triethylsilyloxypentadienyllithium, a Versatile 1, 3??Diene??or Vinyl Ketone??Building Block

…, RL Snowden, DP Simmons

Index: Oppolzer, Wolfgang; Snowden, Roger L.; Simmons, Dana P. Helvetica Chimica Acta, 1981 , vol. 64, # 7 p. 2002 - 2021

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Citation Number: 82

Abstract

Abstract Deprotonation of the 3-trialkylsilyloxy-1, 4-diene 3a and subsequent electrophilic substitution of the non-isolated 3-trialkylsilyoxypentadienyllithium 4 gives the α-and γ- products 8 and/or 6 in good yields. Whereas alkylation of 4 proceeds with variable regioselectivity (Table 1) aldehydes and ketones attack preferentially the γ-position of 4 (Table 2). The desired γ-products 6 may be directly subjected to inter-and intramolecular [ ...

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