Stereoselective Access to Diverse Alkaloid-like Scaffolds via an Oxidation/Double-Mannich Reaction Sequence

Charlie Mikan; Joseph Watson; Ryan Walton; Paul Waddell; Jonathan Knowles

doi:10.1021/acs.orglett.4c01924

Stereoselective Access to Diverse Alkaloid-like Scaffolds via an Oxidation/Double-Mannich Reaction Sequence

Charlie Mikan, Joseph Watson, Ryan Walton, Paul Waddell, Jonathan Knowles^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

50 Downloads (Pure)

Abstract

Sequential oxidative cleavage and double-Mannich reactions enable the stereoselective conversion of simple norbornenes into complex alkaloid-like structures. The products undergo a wide range of derivatization reactions, including regioselective enol triflate formation/cross-coupling sequences and highly efficient conversion to an unusual tricyclic 8,5,5-fused lactam. Overall, the process represents a formal one-atom aza-ring expansion with concomitant bridging annulation, making it of interest for the broader derivatization of alkene feedstocks.

Original language	English
Pages (from-to)	5549–5553
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	26
Early online date	21 Jun 2024
DOIs	https://doi.org/10.1021/acs.orglett.4c01924
Publication status	Published - 5 Jul 2024

Keywords

amides
amines
hydrocarbons
organic compounds
scaffolds

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10.1021/acs.orglett.4c01924Licence: CC BY

mikan-et-al-2024-stereoselective-access-to-diverse-alkaloid-like-scaffolds-via-an-oxidation-double-mannich-reactionFinal published version, 1.71 MBLicence: CC BY

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title = "Stereoselective Access to Diverse Alkaloid-like Scaffolds via an Oxidation/Double-Mannich Reaction Sequence",

abstract = "Sequential oxidative cleavage and double-Mannich reactions enable the stereoselective conversion of simple norbornenes into complex alkaloid-like structures. The products undergo a wide range of derivatization reactions, including regioselective enol triflate formation/cross-coupling sequences and highly efficient conversion to an unusual tricyclic 8,5,5-fused lactam. Overall, the process represents a formal one-atom aza-ring expansion with concomitant bridging annulation, making it of interest for the broader derivatization of alkene feedstocks.",

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AU - Mikan, Charlie

AU - Watson, Joseph

AU - Walton, Ryan

AU - Waddell, Paul

AU - Knowles, Jonathan

PY - 2024/7/5

Y1 - 2024/7/5

N2 - Sequential oxidative cleavage and double-Mannich reactions enable the stereoselective conversion of simple norbornenes into complex alkaloid-like structures. The products undergo a wide range of derivatization reactions, including regioselective enol triflate formation/cross-coupling sequences and highly efficient conversion to an unusual tricyclic 8,5,5-fused lactam. Overall, the process represents a formal one-atom aza-ring expansion with concomitant bridging annulation, making it of interest for the broader derivatization of alkene feedstocks.

AB - Sequential oxidative cleavage and double-Mannich reactions enable the stereoselective conversion of simple norbornenes into complex alkaloid-like structures. The products undergo a wide range of derivatization reactions, including regioselective enol triflate formation/cross-coupling sequences and highly efficient conversion to an unusual tricyclic 8,5,5-fused lactam. Overall, the process represents a formal one-atom aza-ring expansion with concomitant bridging annulation, making it of interest for the broader derivatization of alkene feedstocks.

KW - amides

KW - amines

KW - hydrocarbons

KW - organic compounds

KW - scaffolds

UR - https://www.scopus.com/pages/publications/85196943220

U2 - 10.1021/acs.orglett.4c01924

DO - 10.1021/acs.orglett.4c01924

M3 - Article

SN - 1523-7060

VL - 26

SP - 5549

EP - 5553

JO - Organic Letters

JF - Organic Letters

IS - 26

ER -

Stereoselective Access to Diverse Alkaloid-like Scaffolds via an Oxidation/Double-Mannich Reaction Sequence

Abstract

Keywords

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