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Rearrangement of N-tert-butanesulfinyl α-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected α-amino carbonyl compounds

(2012) JOURNAL OF ORGANIC CHEMISTRY. 77(14). p.6023-6032
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Abstract
Reaction of N-tert-butanesulfinyl alpha-halo imines with alkoxides afforded new N-tert-butanesulfinyl 2-amino acetals in good to excellent yield. These N-tert-butanesulfinyl 2-amino acetals are convenient precursors for the TMSOTf-promoted synthesis of the corresponding N-protected alpha-amino aldehydes and ketones, as well as for the HCl-promoted synthesis of 2-amino acetal hydrochlorides and alpha-amino ketone and alpha-amino aldehyde hydrochlorides in high yield. Via this method, an asymmetric synthesis of (S)-cathinone hydrochloride (er 94:6) was achieved.
Keywords
ALDEHYDES, REACTIVITY, KETONES, ALPHA, CHLORO KETIMINES, ORGANIC-SYNTHESIS, MEDIATED ASYMMETRIC-SYNTHESIS, NEBER REARRANGEMENT, SUBSTITUTED AZIRIDINES, ENANTIOSELECTIVE SYNTHESIS, BETA-EPOXY SULFOXIDES

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Citation

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Chicago
Colpaert, Filip, Sven Mangelinckx, Bram Denolf, and Norbert De Kimpe. 2012. “Rearrangement of N-tert-butanesulfinyl Α-halo Imines with Alkoxides to N-tert-butanesulfinyl 2-amino Acetals as Precursors of N-protected and N-unprotected Α-amino Carbonyl Compounds.” Journal of Organic Chemistry 77 (14): 6023–6032.
APA
Colpaert, F., Mangelinckx, S., Denolf, B., & De Kimpe, N. (2012). Rearrangement of N-tert-butanesulfinyl α-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected α-amino carbonyl compounds. JOURNAL OF ORGANIC CHEMISTRY, 77(14), 6023–6032.
Vancouver
1.
Colpaert F, Mangelinckx S, Denolf B, De Kimpe N. Rearrangement of N-tert-butanesulfinyl α-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected α-amino carbonyl compounds. JOURNAL OF ORGANIC CHEMISTRY. 2012;77(14):6023–32.
MLA
Colpaert, Filip, Sven Mangelinckx, Bram Denolf, et al. “Rearrangement of N-tert-butanesulfinyl Α-halo Imines with Alkoxides to N-tert-butanesulfinyl 2-amino Acetals as Precursors of N-protected and N-unprotected Α-amino Carbonyl Compounds.” JOURNAL OF ORGANIC CHEMISTRY 77.14 (2012): 6023–6032. Print.
@article{3263271,
  abstract     = {Reaction of N-tert-butanesulfinyl alpha-halo imines with alkoxides afforded new N-tert-butanesulfinyl 2-amino acetals in good to excellent yield. These N-tert-butanesulfinyl 2-amino acetals are convenient precursors for the TMSOTf-promoted synthesis of the corresponding N-protected alpha-amino aldehydes and ketones, as well as for the HCl-promoted synthesis of 2-amino acetal hydrochlorides and alpha-amino ketone and alpha-amino aldehyde hydrochlorides in high yield. Via this method, an asymmetric synthesis of (S)-cathinone hydrochloride (er 94:6) was achieved.},
  author       = {Colpaert, Filip and Mangelinckx, Sven and Denolf, Bram and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  language     = {eng},
  number       = {14},
  pages        = {6023--6032},
  title        = {Rearrangement of N-tert-butanesulfinyl \ensuremath{\alpha}-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected \ensuremath{\alpha}-amino carbonyl compounds},
  url          = {http://dx.doi.org/10.1021/jo300752c},
  volume       = {77},
  year         = {2012},
}

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