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The chiral complexing reagent 1 used in the reductive cyclization of 3-(ω-iodoalkylidene)piperidin-2-ones in the presence of Bu3SnH and with BEt3 as the initiator (see scheme) leads to good enantioselectivities thanks to its hydrogen bond mediated association with the radical intermediate. As this example shows, high stereoselectivities are possible for radical reactions proceeding through H-bonded intermediates.
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Aechtner et al. (2004) studied this question.
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