The first organocatalyst-mediated enantioselective substitution of racemic iodoalkanes under radical conditions

We have demonstrated for the first time an organocatalyst-mediated enantioselective substitution of racemic iodoalkanes at either a tertiary or a secondary stereogenic center leading to the corresponding optically active products with a tertiary or a quaternary allylated stereogenic center under radical conditions.

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(S)-3-PropyldihydrocoumarinC12H14O2Ee = 61%[α]D = −12.4 (c 1.25, CHCl3)Source of chirality: enantioselective reactionAbsolute configuration: (S)

(S)-2-Benzyl-3-toluenesulfonyloxypropyl acetateC19H22O5SEe: not determined[α]D = +4.8 (c 1.13, CHCl3)Source of chirality: (R)-2-benzyl-3-hydroxypropylAbsolute configuration: (S)

(S)-2-BenzylpentanolC12H18OEe: not determined[α]D = −9.9 (c 1.09, MeOH)Source of chirality: (R)-2-benzyl-3-hydroxypropyl acetateAbsolute configuration: (S)

(S)-2-Benzylpentanoic acidC12H16O2Ee: not determined[α]D = +19.5 (c 2.21, c-hexane)Source of chirality: (R)-2-benzyl-3-hydroxypropylAbsolute configuration: (S)

(S)-2-PropylindanoneC12H14OEe: not determined[α]D = +32.5 (c 0.71, benzene)Source of chirality: (R)-2-benzyl-3-hydroxypropylAbsolute configuration: (S)