Organic Letters p. 2831 - 2835 (2021)
Update date:2022-08-05
Topics:
Yamane, Daichi
Tanaka, Haruna
Hirata, Akihiro
Tamura, Yumiko
Takahashi, Daichi
Takahashi, Yusuke
Nagamitsu, Tohru
Ohtawa, Masaki
A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.
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