A Convenient Preparation of Enantiomerically Pure (+)‐(1 R ,2 R )‐ and (−)‐(1 S ,2 S )‐1,2‐Diamino‐1,2‐diphenylethanes | Zendy

Braddock D. Christopher | Zendy; Redmond Joanna M. | Zendy; Hermitage Stephen A. | Zendy; White Andrew J. P. | Zendy

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A Convenient Preparation of Enantiomerically Pure (+)‐(1 R ,2 R )‐ and (−)‐(1 S ,2 S )‐1,2‐Diamino‐1,2‐diphenylethanes

Author(s) -

Braddock D. Christopher,

Redmond Joanna M.,

Hermitage Stephen A.,

White Andrew J. P.

Publication year - 2006

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200505440

Subject(s) - chemistry , benzaldehyde , benzoic acid , hydrolysis , enantiomer , resolution (logic) , enantiomeric excess , organic chemistry , medicinal chemistry , catalysis , stereochemistry , enantioselective synthesis , artificial intelligence , computer science

A gram‐scale preparation of (1 S ,2 S )‐ and (1 R ,2 R )‐1,2‐diamino‐1,2‐diphenylethanes, (1 S ,2 S )‐ 1 and (1 R ,2 R )‐ 1 , is reported via (±)‐ iso ‐amarine 4 . Strategically, the activation of (±)‐ iso ‐amarine 4 for hydrolysis to the required diamines and enantiomeric resolution is achieved simultaneously by formation of two separable diastereoisomeric N ‐acylamidines 5 and 6 derived from direct DCC‐mediated coupling of (±)‐ iso ‐amarine 4 with ( R )‐acetylmandelic acid. iso ‐Amarine 4 is conveniently obtained from amarine 3 , and a one‐pot synthesis of the latter is reported from benzaldehyde and hexamethyldisilazane as catalysed by benzoic acid.

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