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Stereoselective Reduction of Enaminones to syn γ-Aminoalcohols.

✍ Scribed by Giuseppe Bartoli; Giovanna Cupone; Renato Dalpozzo; Antonio De Nino; Loredana Maiuolo; Antonio Procopio; Antonio Tagarelli

Book ID
101936269
Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
33
Category
Article
ISSN
0931-7597

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✍ Giuseppe Bartoli; Marcella Bosco; Renato Dalpozzo; Enrico Marcantoni; Massimo Ma 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 81 KB

In the presence of titanium tetrachloride, the borane/tetrahydrofuran complex can reduce 2-methyl-3-oxoamides into the corresponding syn-aminols in good yields and high diastereoselectivity. The use of borane/dimethyl sulfide instead of BH 3 /THF allows a partial reduction to syn-b-hydroxyamides.