Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis
نویسندگان
چکیده
منابع مشابه
Asymmetric synthesis of anti-1,2-amino alcohols via the Borono-Mannich reaction: a formal synthesis of (-)-swainsonine.
Chiral alpha-hydroxy aldehydes generated in situ by the ADH reaction of vinyl sulfones undergo a borono-Mannich reaction with beta-styrenyl boronic acid and primary amines to give anti-1,2-amino alcohols in high enantiomeric purities (83-95% ee). This new method allows much more rapid access to these valuable chiral building blocks that has been used in a short formal synthesis (10 synthetic st...
متن کاملSynthesis of enantioenriched 1,2-trans-diamines using the borono-Mannich reaction with N-protected α-amino aldehydes.
The three-component Petasis borono-Mannich reaction starting with easily accessible N-protected α-amino aldehydes produces efficiently and diastereoselectively 1,2-trans-diamines with an enantiomeric excess of up to 98%.
متن کاملGlycerol as an Efficient Medium for the Petasis Borono–Mannich Reaction
The multicomponent Petasis borono-Mannich (PBM) reaction is a useful tool for the preparation of complex molecules in a single step from boronic acids, aldehydes/ketones, and amines. Here, we describe the use of glycerol in the PBM reaction of salicylaldehydes or 2-pyridinecarbaldehyde with several boronic acids and secondary amines. From these readily available starting materials, alkylaminoph...
متن کاملRegioselective and diastereoselective borono-Mannich reactions with pinacol allenylboronate.
The first documented study of the borono-Mannich (Petasis) reactions of pinacol allenylboronate is described. The reactions of salicylaldehyde and primary and secondary amines are highly regioselective and give homopropargylamine and α-allenylamine products, respectively. In contrast, glycoaldehyde and chiral α-hydroxyaldehydes give exclusively anti-β-amino-β-allenyl alcohol products, irrespect...
متن کاملThe Redox-Mannich Reaction
A complement to the classic three-component Mannich reaction, the redox-Mannich reaction, utilizes the same starting materials but incorporates an isomerization step that enables the facile preparation of ring-substituted β-amino ketones. Reactions occur under relatively mild conditions and are facilitated by benzoic acid.
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ژورنال
عنوان ژورنال: Pure and Applied Chemistry
سال: 2008
ISSN: 1365-3075,0033-4545
DOI: 10.1351/pac200880040751