Asymmetric Synthesis of Seven‐ and More‐Membered Ring Heterocycles

Troin, Yves; Sinibaldi, Marie‐Eve

doi:10.1002/9783527625505.ch4

Asymmetric Synthesis of Nitrogen Heterocycles 2009

DOI: 10.1002/9783527625505.ch4

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Asymmetric Synthesis of Seven‐ and More‐Membered Ring Heterocycles

Yves Troin

Marie‐Eve Sinibaldi

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Cited by 4 publications

(1 citation statement)

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“…Ring-closing metathesis (RCM) reactions 1 have enabled advances in materials science, 2 chemical biology, 3 natural product, 4 medicinal, 5 and diversity-oriented synthetic chemistry. 6 However, in efforts to synthesize macrocyclic compounds via RCM reactions, control of the stereochemistry of the resulting olefin is often problematic (Scheme 1, A).…”

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confidence: 99%

Control of Olefin Geometry in Macrocyclic Ring-Closing Metathesis Using a Removable Silyl Group

et al. 2011

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confidence: 99%

Control of Olefin Geometry in Macrocyclic Ring-Closing Metathesis Using a Removable Silyl Group

et al. 2011

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A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates

et al. 2017

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Free-radical carbo-alkenylation of N-aryl, N-benzyl, and N-phenethyl-ene-carbamates with a disulfone provides vinylsulfones which may then be functionalized and engaged in Heck-type coupling to furnish highly substituted 5-, 6-and 7-membered nitrogen heterocycles. Grignardmediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the aspidosperma family.

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Sn−Li Transmetalation of α‐Aminoorganostannanes for the Stereoselective Synthesis of Substituted Dehydropiperidines and Dehydroazepanes

et al. 2019

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A highly diastereoselective synthesis of (R,S) or (S,S) 2,6-disubstituted dehydropiperidines and 2,7-disubstituted dehydroazepanes has been developed. The stereochemical preference for the (R,S) or the (S,S) isomer is governed by a tin-lithium exchange/electrophilic trapping sequence combined with a ring-closing metathesis. Their relative order was found to have a dramatic influence on the interaction controlling the epimerization at the anionic center. In each case, the complete stereodivergence of the reactions sequence is explained by considering the stabilization brought by the lithium-carbonyl coordination and rationalized by DFT calculations.

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Asymmetric Synthesis of Seven‐ and More‐Membered Ring Heterocycles

Cited by 4 publications

References 152 publications

Control of Olefin Geometry in Macrocyclic Ring-Closing Metathesis Using a Removable Silyl Group

Control of Olefin Geometry in Macrocyclic Ring-Closing Metathesis Using a Removable Silyl Group

A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates

Sn−Li Transmetalation of α‐Aminoorganostannanes for the Stereoselective Synthesis of Substituted Dehydropiperidines and Dehydroazepanes

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