Journal of Organic Chemistry p. 1256 - 1261 (1987)
Update date:2022-08-05
Topics: Triethylamine Stereoselective Ring Opening Reaction N-chlorosuccinimide
Takaki, Ken
Yasumura, Masateru
Tamura, Takao
Negoro, Kenji
Treatment of 2-<1-(phenylthio)benzyl>cyclohexanol (2c) with N-chlorosuccinimide (NCS) and triethylamine gave various product 3-6c depending on reaction conditions.Exclusive ring-opening reaction of 2c was achieved by temperature control.Thus, five-, six-, and seven-membered cycloalkanols 2a-g were converted to ω-oxo-α,β-unsaturated sulfides 6a-g in good yields.The stereochemistry of the reaction was determined by using four diastereomers 10a-d; trans-erythro-10b and cis-threo-10c afforded (E)- and (Z)-heptenals 6c as a single isomer, respectively, while a mixture of the two isomers 6c (60:40 or 40:60) was obtained from trans-threo-10a and cis-erythro-10d.Allyl-, propargyl-, and <(trimethylsilyl)methyl>cyclohexanols 23, 25, and 27 also yielded corresponding unsaturated sulfides 24, 26, and 28.
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