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Synlett 2001; 2001(11): 1802-1804
DOI: 10.1055/s-2001-18102
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A Novel Preparation of Allylic Trichlorotins from α,α-Diisopropylhomoallylic Alcohols and Its Application to Carbonyl Allylations

Yoshiro Masuyama* , Keisuke Saeki, Sachiko Horiguchi, Yasuhiko Kurusu
  • *Department of Chemistry, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan; Fax + 81(3)32 38 33 61; E-mail: y-masuya@sophia.ac.jp
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Publication Date:
29 October 2001 (online)

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α,α-Diisopropylhomoallylic alcohols react with tin(II) chloride and NCS in CH2Cl2 at -40 °C to -60 °C to produce allylic tins and diisopropyl ketone, and the allylic tins in situ cause nucleophilic addition to aldehydes to afford α-substituted homoallylic alcohols.

nucleophilic additions - allylations - organometallic reagents - allylic tins - homoallylic alcohols