Highly diastereoselective anti-dihydroxylation of 3-N,N-dibenzylaminocyclohex-1-ene N-oxide.

Aciro C.; Davies SG.; Kurosawa W.; Roberts PM.; Russell AJ.; Thomson JE.

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Highly diastereoselective anti-dihydroxylation of 3-N,N-dibenzylaminocyclohex-1-ene N-oxide.

Aciro C., Davies SG., Kurosawa W., Roberts PM., Russell AJ., Thomson JE.

Oxidation of 3-N,N-dibenzylaminocyclohex-1-ene N-oxide in the presence of Cl3CCO2H proceeds with high levels of anti-diastereoselectivity (97% de), with no competing side reactions, allowing access to 1,2-anti-2,3-anti-3-aminocyclohexane-1,2-diol after deprotection.

Original publication

DOI

10.1021/ol900114b

Type

Journal article

Journal

Org Lett

Publication Date

19/03/2009

Volume

Pages

1333 - 1336