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Exploiting 1,2-asymmetric induction in a new chiral auxiliary strategy

June 17, 2024

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     Exploiting 1,2-asymmetric induction in a new chiral auxiliary strategy 

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    (S)-2-(Dibenzylamino)-3-phenylpropanal as a chiral auxiliary: A new strategy for the asymmetric synthesis of 2-substituted alcohols

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    Scheme 1

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    We set out to avoid the problem of spatial separation between the auxiliary and new stereogenic center by developing a new chiral auxiliary strategy that would exploit the high levels of 1,2-asymmetric induction characteristic of nucleophilic additions to some chiral aldehydes.2 Our plan is outlined in Scheme 1.

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