Tropane and Related Alkaloid Skeletons via a Radical [3+3]-Annulation Process
Keyword(s):
A mild and simple protocol for the synthesis of 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane derivatives is described. It provides these valuable bicyclic alkaloid skeletons in good yields and high levels of diastereoselectivity from simple and readily available starting materials using visible-light photoredox catalysis. This unprecedented annulation process takes advantage of the unique reactivity of ethyl 2-(acetoxymethyl)acrylate as a 1,3-bis radical acceptor and of cyclic N,N-dialkylanilines as radical 1,3-bis radical donors. The success of this process relies on efficient electron transfer processes and highly selective deprotonation of aminium radical cations leading to the key α-amino radical intermediates.
2021 ◽
1969 ◽
Vol 91
(14)
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pp. 3967-3968
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2018 ◽
Vol 43
(4)
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pp. 2207-2211
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1996 ◽
Vol 100
(17)
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pp. 7097-7105
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2014 ◽
Vol 118
(21)
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pp. 3775-3786
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