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Asymmetric synthesis of α-alkylated N-sulfinyl imidates as new chiral building blocks

Filip Colpaert (UGent) , Sven Mangelinckx (UGent) , Guido Verniest (UGent) and Norbert De Kimpe (UGent)
(2009) JOURNAL OF ORGANIC CHEMISTRY. 74(10). p.3792-3797
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Abstract
alpha-Alkylation of N-sulfinyl imidates, prepared via condensation of tert-butanesulfinamide with ortho esters, led to alpha-substituted N-sulfinyl imidates in good-to-excel lent diastereomeric ratios (dr up to > 99: 1) and yields. Deprotection of the alkylated N-sulfinyl imidates gave access to the corresponding imidate hydrochlorides in outstanding yields. These imidate hydrochlorides proved to be excellent intermediates for an easy transformation to chiral amides in good yields and enantiomeric excess upon simple heating in chloroform. Hydrolysis of the alpha-benzylated imidate hydrochlorides afforded the corresponding chiral esters with >95% ee.
Keywords
AGENTS, AMINES, TERT-BUTANESULFINYL IMINES, PRODRUG FORM, ESTER FUNCTION, SULFONAMIDE GROUP, SULFUR-NITROGEN, DERIVATIVES, CHEMISTRY, LIGANDS

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Citation

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Chicago
Colpaert, Filip, Sven Mangelinckx, Guido Verniest, and Norbert De Kimpe. 2009. “Asymmetric Synthesis of Α-alkylated N-sulfinyl Imidates as New Chiral Building Blocks.” Journal of Organic Chemistry 74 (10): 3792–3797.
APA
Colpaert, F., Mangelinckx, S., Verniest, G., & De Kimpe, N. (2009). Asymmetric synthesis of α-alkylated N-sulfinyl imidates as new chiral building blocks. JOURNAL OF ORGANIC CHEMISTRY, 74(10), 3792–3797.
Vancouver
1.
Colpaert F, Mangelinckx S, Verniest G, De Kimpe N. Asymmetric synthesis of α-alkylated N-sulfinyl imidates as new chiral building blocks. JOURNAL OF ORGANIC CHEMISTRY. 2009;74(10):3792–7.
MLA
Colpaert, Filip et al. “Asymmetric Synthesis of Α-alkylated N-sulfinyl Imidates as New Chiral Building Blocks.” JOURNAL OF ORGANIC CHEMISTRY 74.10 (2009): 3792–3797. Print.
@article{628953,
  abstract     = {alpha-Alkylation of N-sulfinyl imidates, prepared via condensation of tert-butanesulfinamide with ortho esters, led to alpha-substituted N-sulfinyl imidates in good-to-excel lent diastereomeric ratios (dr up to {\textrangle} 99: 1) and yields. Deprotection of the alkylated N-sulfinyl imidates gave access to the corresponding imidate hydrochlorides in outstanding yields. These imidate hydrochlorides proved to be excellent intermediates for an easy transformation to chiral amides in good yields and enantiomeric excess upon simple heating in chloroform. Hydrolysis of the alpha-benzylated imidate hydrochlorides afforded the corresponding chiral esters with {\textrangle}95\% ee.},
  author       = {Colpaert, Filip and Mangelinckx, Sven and Verniest, Guido and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  language     = {eng},
  number       = {10},
  pages        = {3792--3797},
  title        = {Asymmetric synthesis of \ensuremath{\alpha}-alkylated N-sulfinyl imidates as new chiral building blocks},
  url          = {http://dx.doi.org/10.1021/jo900046t},
  volume       = {74},
  year         = {2009},
}

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