Abstract
We report a multi‐component asymmetric Brønsted acid‐catalyzed aza‐Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho‐tert‐butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61–98 %) and mostly >90 % optically active cis‐aziridines. (+)‐Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.
Highlights
We report a multi-component asymmetric Brønsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes
Such is the versatility of organocatalysis and its ability to mediate a plethora of diverse reaction types[1] it is, an indispensable “tool” in the synthetic chemists “toolbox”.[2]
Improving atom- and reaction-efficiency is a key driver to developing new reactions and protocols; in this context organocatalysis has demonstrated its importance by efficiently mediating many different convergent reactions or multi-component syntheses
Summary
We report a multi-component asymmetric Brønsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Using a BINOL N-triflylphosphoramide Brønsted acid a 61–98 % yielding asymmetric aza-Darzens reaction affords N-aryl-cis-aziridines in, mostly, 90–99 % ee.
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