O o h o o h2 pdc oh ho o o o o h purpose of

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Unformatted text preview: etals will be hydrolysed at pH 5.5 to give the amine a choice ■ This problem is based on work between cyclisation to one or other of the two aldehydes. OMe MeO by G. W. Gribble and R. M. Soll, J. Org. Chem., 1981, 46, 2433. O N H 2 OMe pH 5.5 OMe H4 3 1 N H 4 2 5 H 3 O Cyclisation to a five- membered ring is preferred to cyclisation to a (strained) four- membered ring so reductive amination occurs to the right and not to the left (as drawn). Cyanoborohydride is stable under the weakly acidic conditions and does not reduce the remaining aldehyde. 5 6 Solutions Manual to accompany Organic Chemistry 2e O H Na(CN)BH3 H N H N OHC O O PROBLEM 7 Account for the chemoselectivity of the first reaction and the stereoselectivity...
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This document was uploaded on 02/10/2014.

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