Diastereoselective Ethynylation of Chiral α‐(Dibenzylamino) Aldehydes: Synthesis of  meso ‐ and Homochiral  C  2 ‐Symmetrical 1,6‐Diamino‐2,5‐diols | Zendy

Andrés José M. | Zendy; Pedrosa Rafael | Zendy; PérezEncabo Alfonso | Zendy

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Diastereoselective Ethynylation of Chiral α‐(Dibenzylamino) Aldehydes: Synthesis of meso ‐ and Homochiral C 2 ‐Symmetrical 1,6‐Diamino‐2,5‐diols

Author(s) -

Andrés José M.,

Pedrosa Rafael,

PérezEncabo Alfonso

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200600214

Subject(s) - chemistry , enantiopure drug , diastereomer , bromide , stereochemistry , organic chemistry , enantioselective synthesis , medicinal chemistry , catalysis

Homochiral α‐(dibenzylamino) aldehydes, prepared from the corresponding α‐amino acids, react with ethynylmagnesium bromide in THF/Et 2 O at 0 °C to afford, in good yields and dr , propargylic 1,2‐amino alcohols; anti diastereomers were always formed as the major products in this reaction. These compounds are versatile intermediates in the synthesis of meso ‐ and enantiopure 1,6‐diamino‐2,5‐diols with C 2 symmetry. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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