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3 = -1.24°.
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note
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2 in the reactant complex (+0.04 vs +0.17 in 11, Table S3; see the Supporting Information) would account for a less favorable electrostatic interaction with nucleophilic carbonyl oxygen and a higher energy transition state for acyl migration step as the first step.
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59
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23144446450
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note
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Optimized structures for this mechanistic proposal are given in the Supporting Information.
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3 = -2.07°.
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This mechanism has also been proposed by other authors, (a) For Rh(I)-catalyzed cycloisomerization of enynes for the preparation of functionalized lactams, see ref 5c.
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A detailed analysis of the overall mechanism, which also accounts for the preferential abstraction of hydrogen from the trans allylic position in the intermediate 21, is provided as part of the Supporting Information.
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Reed, A.E.1
Curtiss, L.A.2
Weinhold, F.3
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