We have developed a highly enantioselective synthesis of syn-a-methyl-�-hydroxy morpholine amides 4  from achiral and chiral aldehydes via the hydroboration of 4-acryloylmorpholine 1  with diisopinocampheylborane. This reaction produces the Z-(diisopinocampheyl)enolborane 2Z with excellent selectivity, which undergoes highly enantioselective aldol reactions with achiral aldehydes (>96% ee) and equally diastereoselective double asymmetric reactions with a range of chiral aldehydes (d.r. >20:1).This simple method is exceptionally cost-effective. It is noteworthy that the enantioselectivity of these reactions is greater than that achieved in the vast majority of diisopinocampheylborane-mediated aldol reactions.Scope, transition states and extensions (anti aldol, construction of all-carbon quaternary stereocenters,...) of this method will be discussed.

(Diisopinocampheyl)borane-mediated reductive aldol reactions: Highly enantio- and diastereoselective synthesis of <i>syn</i>-aldols from <i>N</i>-acryloylmorpholine

246th National Meeting (2013)

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(Diisopinocampheyl)borane-mediated reductive aldol reactions: Highly enantio- and diastereoselective synthesis of syn-aldols from N-acryloylmorpholine