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One-pot highly stereoselective reduction of β-keto amides to syn-γ-aminols

✍ Scribed by Giuseppe Bartoli; Marcella Bosco; Renato Dalpozzo; Enrico Marcantoni; Massimo Massaccesi; Samuele Rinaldi; Letizia Sambri

Book ID
104231949
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
81 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

Highly stereoselective titanium-mediated
Highly stereoselective titanium-mediated addition of organocerium reagents to β-keto amides: an efficient synthesis of stereodefined β-hydroxy amides having a tertiary alcoholic fragment
✍ Giuseppe Bartoli; Marcella Bosco; Enrico Marcantoni; Massimo Massaccesi; Samuele 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 79 KB

A highly efficient and stereoselective protocol for the TiCl 4 -mediated addition of organocerium reagents to b-keto amides is now available. The method allows the introduction of a large variety of carbon frameworks, including primary, secondary and tertiary alkyl chains, as well as aromatic, alkyn