Highly enantioselective organocatalytic α-selenylation of aldehydes using hypervalent iodine compounds

The highly enantioselective organocatalytic α-selenylation reaction of aldehydes using a hypervalent iodine compound as an oxidative agent from commercially available phenyl diselenide under mild oxidative conditions is described. This transformation affords α-selenyl aldehydes in good yields and with excellent enantioselectivities. By using hypervalent iodine compounds, it opens up a suitable and alternative way for the preparation of biologically active building blocks such as β-hydroxy alcohols, α-amino acids, and α-hydroxy esters.

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(R)-3-Methyl-2-(phenylselanyl)butan-1-olC11H16OSe[α]D25=+9.4 (c 0.6, CHCl3)Source of chirality: (5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochlorideAbsolute configuration: (R)

(R)-3,3-Dimethyl-2-(phenylselanyl)butan-1-olC12H18OSe[α]D25=-2.7 (c 1.1, CHCl3)Source of chirality: (5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochlorideAbsolute configuration: (R)

(R)-2-(Phenylselanyl)pentan-1-olC11H16OSe[α]D25=+19.3 (c 0.6, CHCl3)Source of chirality: (5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochlorideAbsolute configuration: (R)

(R)-2-(Phenylselanyl)heptan-1-olC13H20OSe[α]D25=+15.4 (c 0.7, CHCl3)Source of chirality: (5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochlorideAbsolute configuration: (R)

(R)-2-(Phenylselanyl)pent-4-en-1-olC11H14OSe[α]D25=+14.0 (c 0.3, CHCl3)Source of chirality: (5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochlorideAbsolute configuration: (R)

(R)-3-Phenyl-2-(phenylselanyl)propan-1-olC15H16OSe[α]D25=+14.1 (c 0.7, CHCl3)Source of chirality: (5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochlorideAbsolute configuration: (R)

(R)-Benzyl 4-hydroxy-3-(phenylselanyl)butanoateC17H18O3Se[α]D25=+6.8 (c 1.2, CHCl3)Source of chirality: (5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochlorideAbsolute configuration: (R)

Ethyl 2-oxo-1-(phenylselanyl)cyclopentanecarboxylateC14H16O3Se[α]D25=-63.5 (c 1.2, CHCl3)Source of chirality: O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromideAbsolute configuration: unknown