Spirobicyclic diamines 1: synthesis of proline-derived spirolactams via thermal intramolecular ester aminolysis

Fintan Kelleher; Sinead Kelly

doi:10.1016/j.tetlet.2006.03.021

Spirobicyclic diamines 1: synthesis of proline-derived spirolactams via thermal intramolecular ester aminolysis

Fintan Kelleher
, Sinead Kelly

School of Chemical and BioPharmaceutical Science

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

Abstract

Proline-derived [4.4]-spirolactams have been synthesised in good yields by a reductive-amination reaction followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. The synthesis of the corresponding [4.5]-spirolactams by the same method gave much reduced yields.

Original language	English
Pages (from-to)	3005-3008
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2006.03.021
Publication status	Published - 1 May 2006

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title = "Spirobicyclic diamines 1: synthesis of proline-derived spirolactams via thermal intramolecular ester aminolysis",

abstract = "Proline-derived [4.4]-spirolactams have been synthesised in good yields by a reductive-amination reaction followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. The synthesis of the corresponding [4.5]-spirolactams by the same method gave much reduced yields.",

author = "Fintan Kelleher and Sinead Kelly",

note = "Funding Information: We thank Dr. Brian Murray for help with NMR spectroscopy and useful discussions. We are grateful to Strand III of the Irish Government{\textquoteright}s National Development Plan (2000–2006) Technological Sector Research Program, through the Council of Directors of the Institutes of Technology, for funding for S.K. (Grant CRS/01/TA02).",

year = "2006",

month = may,

day = "1",

doi = "10.1016/j.tetlet.2006.03.021",

language = "English",

volume = "47",

pages = "3005--3008",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Spirobicyclic diamines 1

T2 - synthesis of proline-derived spirolactams via thermal intramolecular ester aminolysis

AU - Kelleher, Fintan

AU - Kelly, Sinead

N1 - Funding Information: We thank Dr. Brian Murray for help with NMR spectroscopy and useful discussions. We are grateful to Strand III of the Irish Government’s National Development Plan (2000–2006) Technological Sector Research Program, through the Council of Directors of the Institutes of Technology, for funding for S.K. (Grant CRS/01/TA02).

PY - 2006/5/1

Y1 - 2006/5/1

N2 - Proline-derived [4.4]-spirolactams have been synthesised in good yields by a reductive-amination reaction followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. The synthesis of the corresponding [4.5]-spirolactams by the same method gave much reduced yields.

AB - Proline-derived [4.4]-spirolactams have been synthesised in good yields by a reductive-amination reaction followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. The synthesis of the corresponding [4.5]-spirolactams by the same method gave much reduced yields.

UR - https://www.scopus.com/pages/publications/33645871852

U2 - 10.1016/j.tetlet.2006.03.021

DO - 10.1016/j.tetlet.2006.03.021

M3 - Article

AN - SCOPUS:33645871852

SN - 0040-4039

VL - 47

SP - 3005

EP - 3008

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

Spirobicyclic diamines 1: synthesis of proline-derived spirolactams via thermal intramolecular ester aminolysis

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