New Protocol for Converting Alcohols Into Amines

Klepacz, Anna; Zwierzak, A.

doi:10.1081/scc-100103987

Cited by 8 publications

(4 citation statements)

References 12 publications

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“…The combined organic phases were dried (Na 2 SO 4 ) and the solvent was evaporated under reduced pressure affording optically pure product (S)-2 f as a colorless oil (90 mg, 89 % yield, > 99 % ee); ½a 20 D = 6.8 cm 3 g À1 dm À1 (c = 0.011 g cm À3 in benzene) [lit. ½a 20 D = À5.20 cm 3 g À1 dm À1 (c = 0.02 g cm À3 in benzene), (R)-enantiomer] [51] ; 1 H NMR data were in agreement with literature. [52] For details concerning the sequences of w-transaminases as well as experimental procedures and analytical methods for amines 2 a-f, see the Supporting Information.…”

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confidence: 88%

Synthesis of Optically Active Amines Employing Recombinant ω‐Transaminases in E. coli Cells

et al. 2010

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Various recombinant ω‐transaminases, overexpressed in E. coli cells and employed as whole‐cell catalysts, are tested for the synthesis of enantiomerically pure amines from the corresponding prochiral ketones. Optically pure (S)‐amines are obtained by formal reductive amination, consuming just ammonia and a cheap reducing agent (formate) with up to 99 % ee and 97 % yield. The other enantiomer was accessible by employing the same ω‐transaminases in a kinetic resolution starting from racemic amines. A ω‐transaminase derived from an Arthrobacter species displayed the highest stereoselectivity for all substrates tested, both for the kinetic resolution of rac‐amines and for the amination of ketones.

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confidence: 88%

Synthesis of Optically Active Amines Employing Recombinant ω‐Transaminases in E. coli Cells

et al. 2010

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“…This reaction shows that a phosphoryl group together with another activating group can make nitrogen sufficiently nucleophilic to undergo N-alkylation even with the traditional Ph 3 P-DIAD system. 1005 As was mentioned earlier, the presence of two electronwithdrawing groups on nitrogen should lower the pK a of the N-H bond, and hence, bis-protected hydroxylamines are good Mitsunobu nucleophiles. Many of them were readily prepared by a Schotten-Bauman route in which an ice-cold aqueous THF solution of HONH 2 • HCl containing sodium carbonate was reacted with 2 equiv of the respective chloroformate.…”

Section: N-alkylation With Sulfonamides and Related Nucleophilesmentioning

confidence: 83%

“…The phosphoramidate 326 underwent ready alkylation with n -butanol under Mitsunobu conditions (Scheme ). This reaction shows that a phosphoryl group together with another activating group can make nitrogen sufficiently nucleophilic to undergo N -alkylation even with the traditional Ph 3 P−DIAD system …”

Section: Amines Amides (Including Nucleobases) or Azides As Nucleophilesmentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

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“…1 In an alternative synthesis of this amine and some homologues, 1-halo-2alkynes or analogous acetylenic arenesulfonates were reacted with hexamethylenetetramine, after which the salt was treated with dilute hydrochloric acid. 2 Zwierzak and co-workers [4][5][6][7] developed some substitutes for the synthesis of primary amines among which was 1-amino-2-propyne.…”

mentioning

confidence: 99%