Asymmetric syntheses of N-acetyl-(R)-coniine and N-Boc-(2R,6R)-solenopsin A via ring-closing metathesis

Ramaiah Kumareswaran; Alfred Hassner

doi:10.1016/S0957-4166(01)00411-6

Asymmetric syntheses of N-acetyl-(R)-coniine and N-Boc-(2R,6R)-solenopsin A via ring-closing metathesis

Ramaiah Kumareswaran, Alfred Hassner

Department of Chemistry

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

38 Scopus citations

Abstract

Asymmetric syntheses of piperidine alkaloids N-acetyl-(R)-coniine and (2R,6R)-trans-solenopsin were achieved utilizing stereoselective additions of allylphenylsulfone to chiral alkyl-N-sulfinylimines and ring-closing olefin metathesis.

Original language	English
Pages (from-to)	2269-2276
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	12
Issue number	16
DOIs	https://doi.org/10.1016/S0957-4166(01)00411-6
State	Published - 13 Sep 2001

Bibliographical note

Funding Information:
Support of this research by a grant from the US–Israel Binational Science Foundation and from the Marcus Center for Medicinal and Pharmaceutical Chemistry is gratefully acknowledged. We thank Professor A. I. Meyers for providing (S)-coniine·HCl as well as HPLC analysis of 12 and 13 , and Dr. H. E. Gottlieb for valuable help with NMR spectra.

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10.1016/S0957-4166(01)00411-6

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title = "Asymmetric syntheses of N-acetyl-(R)-coniine and N-Boc-(2R,6R)-solenopsin A via ring-closing metathesis",

abstract = "Asymmetric syntheses of piperidine alkaloids N-acetyl-(R)-coniine and (2R,6R)-trans-solenopsin were achieved utilizing stereoselective additions of allylphenylsulfone to chiral alkyl-N-sulfinylimines and ring-closing olefin metathesis.",

author = "Ramaiah Kumareswaran and Alfred Hassner",

note = "Funding Information: Support of this research by a grant from the US–Israel Binational Science Foundation and from the Marcus Center for Medicinal and Pharmaceutical Chemistry is gratefully acknowledged. We thank Professor A. I. Meyers for providing (S)-coniine·HCl as well as HPLC analysis of 12 and 13 , and Dr. H. E. Gottlieb for valuable help with NMR spectra.",

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AU - Hassner, Alfred

N1 - Funding Information: Support of this research by a grant from the US–Israel Binational Science Foundation and from the Marcus Center for Medicinal and Pharmaceutical Chemistry is gratefully acknowledged. We thank Professor A. I. Meyers for providing (S)-coniine·HCl as well as HPLC analysis of 12 and 13 , and Dr. H. E. Gottlieb for valuable help with NMR spectra.

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AB - Asymmetric syntheses of piperidine alkaloids N-acetyl-(R)-coniine and (2R,6R)-trans-solenopsin were achieved utilizing stereoselective additions of allylphenylsulfone to chiral alkyl-N-sulfinylimines and ring-closing olefin metathesis.

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Asymmetric syntheses of N-acetyl-(R)-coniine and N-Boc-(2R,6R)-solenopsin A via ring-closing metathesis

Abstract

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