Spirobicyclic diamines. Part 2: Synthesis of homochiral diastereoisomeric proline derived [4.4]-spirolactams

Fintan Kelleher; Sinead Kelly

doi:10.1016/j.tetlet.2006.05.154

Spirobicyclic diamines. Part 2: Synthesis of homochiral diastereoisomeric proline derived [4.4]-spirolactams

Fintan Kelleher, Sinead Kelly

School of Chemical and BioPharmaceutical Science

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

Abstract

l-Proline derived diastereoisomeric [4.4]-spirolactams have been prepared by a reductive-amination reaction of (R)- or (S)-alanine methyl ester, followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. Under similar conditions (R)- or (S)-phenylalanine methyl ester gave no cyclisation products, while R- or S-α-methylbenzylamine required treatment with NaNH₂ in refluxing toluene to induce cyclisation giving diastereoisomeric [4.4]-spirolactams.

Original language	English
Pages (from-to)	5247-5250
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2006.05.154
Publication status	Published - 24 Jul 2006

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title = "Spirobicyclic diamines. Part 2: Synthesis of homochiral diastereoisomeric proline derived [4.4]-spirolactams",

abstract = "l-Proline derived diastereoisomeric [4.4]-spirolactams have been prepared by a reductive-amination reaction of (R)- or (S)-alanine methyl ester, followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. Under similar conditions (R)- or (S)-phenylalanine methyl ester gave no cyclisation products, while R- or S-α-methylbenzylamine required treatment with NaNH2 in refluxing toluene to induce cyclisation giving diastereoisomeric [4.4]-spirolactams.",

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). ",

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doi = "10.1016/j.tetlet.2006.05.154",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Spirobicyclic diamines. Part 2

T2 - Synthesis of homochiral diastereoisomeric proline derived [4.4]-spirolactams

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 - 2006/7/24

Y1 - 2006/7/24

N2 - l-Proline derived diastereoisomeric [4.4]-spirolactams have been prepared by a reductive-amination reaction of (R)- or (S)-alanine methyl ester, followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. Under similar conditions (R)- or (S)-phenylalanine methyl ester gave no cyclisation products, while R- or S-α-methylbenzylamine required treatment with NaNH2 in refluxing toluene to induce cyclisation giving diastereoisomeric [4.4]-spirolactams.

AB - l-Proline derived diastereoisomeric [4.4]-spirolactams have been prepared by a reductive-amination reaction of (R)- or (S)-alanine methyl ester, followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. Under similar conditions (R)- or (S)-phenylalanine methyl ester gave no cyclisation products, while R- or S-α-methylbenzylamine required treatment with NaNH2 in refluxing toluene to induce cyclisation giving diastereoisomeric [4.4]-spirolactams.

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U2 - 10.1016/j.tetlet.2006.05.154

DO - 10.1016/j.tetlet.2006.05.154

M3 - Article

AN - SCOPUS:33745223861

SN - 0040-4039

VL - 47

SP - 5247

EP - 5250

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

Spirobicyclic diamines. Part 2: Synthesis of homochiral diastereoisomeric proline derived [4.4]-spirolactams

Abstract

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