- Amine-directed hydroboration: Scope and limitations
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Iodine activation induces intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes with good to excellent control of regiochemistry compared to control experiments using excess THF?BH3. Deuterium labeling and other evidence confirm that the iodine-induced hydroboration reaction of homoallylic amine boranes occurs via an intramolecular mechanism equivalent to the classical 4-center process and without competing retro-hydroboration. Longer carbon chain tethers result in lower regioselectivity, whereas the shorter tether in allylic amines results in a switch to dominant intermolecular hydroboration. Regioselectivity in THF?BH3 control experiments is higher for the allylic amine boranes compared to the iodine activation experiments, whereas the reverse is true for homoallylic amine borane activation.
- Scheideman, Matthew,Wang, Guoqiang,Vedejs, Edwin
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p. 8669 - 8676
(2009/02/03)
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- A versatile method for the synthesis of cis-2-aminomethylcyclanols
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Reduction of cis-2-phenyl-4a,5,6,7,8,8a-hexahydro-4H-1,3-benzoxazine and its homologue derivatives 1-4 resulted in N-benzyl- or N-unsubstituted alicyclic 1,3-amino alcohols 5-12, depending on the conditions used.
- Fueloep, Ferenc,Simon, Lajos,Simon-Talpas, Gizella,Bernath, Gabor
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p. 2303 - 2310
(2007/10/03)
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- trans-2-Cyanocycloalkanols: Versatile Synthons for Alicyclic cis- and trans-1,3-Amino Alcohols
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From trans-2-hydroxycyclopentanecarbonitrile (1) and trans-2-hydroxycyclohexanecarbonitrile (2), a number of trans-2-aminomethylcycloalkanols are prepared by reductive alkylation.Inversion of trans-N-acylaminocycloalkanols by treatment with thionyl chlori
- Fueloep, Ferenc,Huber, Imre,Bernath, Gabor,Hoenig, Helmut,Seufer-Wasserthal, Peter
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- STEREOCHEMICAL STUDIES, 80. CYCLIC AMINOALCOHOLS AND RELATED COMPOUNDS, 26. PREPARATION OF CIS-2-(ALKYLAMINOMETHYL)- AND (ARALKYLAMINOMETHYL)-1-CYCLANOLS FROM OLEFINS VIA THE 5,6-DIHYDRO-4H-1,3-OXAZINE DERIVATIVES
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Cycloalkenes were allowed to react with N-(hydroxymethyl)alkyl- or -arylamides in the presence of concentrated sulfuric acid in glacial acetic acid, using the method suggested by Schmidt.In the majority of cases, the reaction yielded the corresponding cis
- Simon, Lajos,Talpas, Gizella S.,Fueloep, Ferenc,Bernath, Gabor
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p. 139 - 146
(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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