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1 article(s) from Penner, Anna

2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β²-amino acids

Markus Nahrwold,
Arvydas Stončius,
Anna Penner,
Beate Neumann,
Hans-Georg Stammler and
Norbert Sewald

Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43

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Scheme 1: Selectively cleavable β²-amino acid precursors: Structures and reactivities of 2-tert-butyl-tetrahy...

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Scheme 2: Cyclocondensation of Cbz-^βAla-NH₂ (3) and benzaldehyde. a) [p-TsOH], toluene, reflux, Dean–Stark tr...

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Scheme 3: Protection and deprotection of 4. a) Boc₂O, DMAP, CH₃CN, 16 h, rt; b) 1. n-BuLi, THF, −78 °C, 30 mi...

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Scheme 4: Synthesis of enantiopure 2-phenyl-tetrahydropyrimidine-4(1H)-ones. a) PhCH(OMe)₂, BF₃·Et₂O (6.0 equ...

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Figure 1: X-ray crystal structure of 10 [44].

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Scheme 5: Diastereoselective alkylation of 5.

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Figure 2: Comparison of coupling constants (C⁵–C⁶-ABX system) within the ¹H-NMR spectra of literature known c...

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Figure 3: Supposed enolate conformations.

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Scheme 6: Selective ring opening of the heterocycle 11d and isolation of orthogonally protected β²-homoaspart...

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Published 14 Sep 2009

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2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β²-amino acids