- Chemo- and diastereoselective reduction of β-enamino esters: A convenient synthesis of both cis- and trans-γ-amino alcohols and β-amino esters
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Convenient procedures for the chemo- and diastereoselective reduction of b-enamino esters 1 are described. Both cis- and trans-γ-amino alcohols 2 or b-amino esters 3 can be prepared by reduction of b-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Na/i-PrOH or NaHB(OAc)3/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric γ-amino alcohols 2 and β-amino esters 3 obtained are established by 1H and 13C NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.
- Bartoli,Cimarelli,Marcantoni,Palmieri,Petrini
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p. 5328 - 5335
(2007/10/02)
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- Preparations and Crystal Structures of the 2-Oxides of Some Octahydro-3,2,1-benzoxathiazines and Octahydro-2H-3,1,2-benzoxazaphosphorines
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The cis- and trans-fused 1-benzyl-1,4,4a,5,6,7,8,8a-octahydro-3,2,1-benzoxathiazine 2-oxides and cis- and trans-fused 1-benzyl-2-phenyl-1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphorine 2-oxides have been prepared from the cis- and trans-2-benzylaminocyclohexanemethanols and their structures have been determined by n.m.r. and crystallographic methods.
- Goodridge, Richard J.,Hambley, Trevor W.,Ridley, Damon D.
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p. 591 - 604
(2007/10/02)
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- STEREOCHEMICAL STUDIES-76 SATURATED HETEROCYCLES-63 SYNTHESIS OF CIS- AND TRANS-N-METHYL- AND N-BENZYL-4,5- AND 5,6-TETRAMETHYLENETETRAHYDRO-1,3-OXAZINES; AN X-RAY STUDY OF N-BENZYL-CIS-4,5-TETRAMETHYLENETETRAHYDRO-1,3-OXAZINIUM-PICRATE
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The corresponding cis- and trans-N-methyl- and N-benzyl-5,6- and 4,5-tetramethylenetetrahydro-1,3-oxazines (5a,b-8a,b) were synthesized from cis- and trans-N-methyl- and N-benzyl-2-aminomethyl-1-cyclohexanols (1a,b,2 2a,b), and from cis- and trans-N-methy
- Fulop, Ferenc,Bernath, Gabor,Argay, Gyula,Kalman, Alajos,Sohar, Pal
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p. 2053 - 2060
(2007/10/02)
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- STEREOCHEMICAL STUDIES XXXVIII SATURATED HETEROCYCLES, XIV; SYNTHESIS AND CONFORMATIONAL ANALYSIS OF STEREOISOMERIC CIS- AND TRANS-TETRAMETHYLENETETRAHYDRO-N-METHYL- AND -N-BENZYL-1,3-OXAZINES
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Cis and trans-2-methylaminomethyl- and -benzylaminomethyl-1-cyclohexanol (1-4), as well as cis- and trans-2-hydroxymethyl-1-methylamino- and -benzylamino-cyclohexane (5-8) were allowed to react with p-nitrobenzaldehyde to yield 2-p-nitrophenyl-3-methyl- a
- Gera, L.,Bernath, G.,Sohar, P.
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p. 293 - 302
(2007/10/02)
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