Synthesis of enantioenriched 1,2-trans-diamines using the borono-Mannich reaction with N-protected α-amino aldehydes.
نویسندگان
چکیده
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%.
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...
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متن کاملAmino Acid Based Synthesis of Chiral Long Chain Diamines and Tetramines
A method for the synthesis of long chain diamines and tetramines starting from natural α-amino acids is reported. Diamines and tetramines were prepared through the Wittig olefination reaction of N-protected amino aldehydes obtained from phenylalanine and lysine. A 1,2,17,18-tetramine was synthesized using (2S)-1-azido-2-[bis(tertbutoxycarbonyl)-amino]-5-oxopentane as key-intermediate compound.
متن کاملExpedient synthesis of chiral 1,2- and 1,4-diamines: protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions.
[reaction: see text] Organocatalytic asymmetric Mannich reaction of protected amino ketones with imines in the presence of an L-proline-derived tetrazole catalyst afforded diamines with excellent yields and enantioselectivities of up to 99%. The amino ketone protecting group controlled the regioselectivity of the reaction providing access to chiral 1,2-diamines from azido ketones and 1,4-diamin...
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ورودعنوان ژورنال:
- Chemical communications
دوره 51 49 شماره
صفحات -
تاریخ انتشار 2015