Use of Manganese(V) Nitrides as Enantioselective Nitrogen-Transfer Reagents

Author: Tomooka, Craig Shigeru

Year: 1999

Degree: Master's thesis

Advisor: Carreira, Erick Moran

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/6t7v-s157

Abstract

Once activated, manganese(V) nitrides have been shown to efficiently transfer nitrogen to furanoid. glycals. This process, followed by hydrolysis, forms the corresponding amino alcohols in high yield and diastereoselectivity. The isolation of an intermediate oxazoline and the ability to form this oxazoline from the amino alcohol was also discovered. The formation of chiral manganese nitrides is also described. After considerable experimentation, the transfer of nitrogen in these cases resulted in enantiomeric excesses of up to 92% accompanied by high yields.

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