Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

Fintan Kelleher; Sinead Kelly; Vickie McKee

doi:10.1016/j.tet.2007.06.050

Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

Fintan Kelleher, Sinead Kelly, Vickie McKee

School of Chemical and BioPharmaceutical Science

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

Abstract

The syntheses of racemic and homochiral [4.4]-spirolactams, starting from l-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives a series of homochiral [4.4]-spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded dimeric structure, where the monomers are diastereoisomeric diamines.

Original language	English
Pages (from-to)	9235-9242
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2007.06.050
Publication status	Published - 10 Sep 2007

Keywords

Dimer
Spirodiamines
Spirolactam
Synthesis
X-ray crystal structure

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10.1016/j.tet.2007.06.050

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title = "Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines",

abstract = "The syntheses of racemic and homochiral [4.4]-spirolactams, starting from l-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives a series of homochiral [4.4]-spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded dimeric structure, where the monomers are diastereoisomeric diamines.",

keywords = "Dimer, Spirodiamines, Spirolactam, Synthesis, X-ray crystal structure",

author = "Fintan Kelleher and Sinead Kelly and Vickie McKee",

note = "Funding Information: We thank Dr. Brian Murray for the help with NMR spectroscopy and useful discussions. We are grateful to Kuldip Singh for access to the Apex diffractometer at the University of Leicester, UK. 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). ",

year = "2007",

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doi = "10.1016/j.tet.2007.06.050",

language = "English",

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journal = "Tetrahedron",

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T2 - Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

AU - Kelleher, Fintan

AU - Kelly, Sinead

AU - McKee, Vickie

N1 - Funding Information: We thank Dr. Brian Murray for the help with NMR spectroscopy and useful discussions. We are grateful to Kuldip Singh for access to the Apex diffractometer at the University of Leicester, UK. 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 - 2007/9/10

Y1 - 2007/9/10

N2 - The syntheses of racemic and homochiral [4.4]-spirolactams, starting from l-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives a series of homochiral [4.4]-spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded dimeric structure, where the monomers are diastereoisomeric diamines.

AB - The syntheses of racemic and homochiral [4.4]-spirolactams, starting from l-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives a series of homochiral [4.4]-spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded dimeric structure, where the monomers are diastereoisomeric diamines.

KW - Dimer

KW - Spirodiamines

KW - Spirolactam

KW - Synthesis

KW - X-ray crystal structure

UR - http://www.scopus.com/inward/record.url?scp=34547465681&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2007.06.050

DO - 10.1016/j.tet.2007.06.050

M3 - Article

AN - SCOPUS:34547465681

SN - 0040-4020

VL - 63

SP - 9235

EP - 9242

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

Abstract

Keywords

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