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Asymmetric synthesis of new chiral β-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines

Filip Colpaert (UGent) , Sven Mangelinckx (UGent) and Norbert De Kimpe (UGent)
(2010) ORGANIC LETTERS. 12(9). p.1904-1907
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Organization
Abstract
New chiral beta-(sulfonylamino)sulfinylimidates are synthesized in high overall yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of chiral N-tert-butanesulfinyl imidates with N-tosyl aldimines. Deprotection of the beta-(sulfonylamino)sulfinylimidates gave access to enantiopure imidate hydrochlorides in high yields, as useful intermediates for an easy transformation to new chiral beta-sulfonylamino amides upon simple heating in chloroform. Hydrolysis of the imidate hydrochlorides afforded the corresponding chiral beta-sulfonylamino esters with >98% ee as new chiral beta-amino acid derivatives.
Keywords
CATALYTIC ADDITION, SULFINIMINES, 3-AMINO ALCOHOLS, ADDITION-REACTIONS, ANTI-1, SYN-1, 3-AMINO, DESIGN, ESTER, ANALOGS, ACTIVATED IMINES

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Citation

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Chicago
Colpaert, Filip, Sven Mangelinckx, and Norbert De Kimpe. 2010. “Asymmetric Synthesis of New Chiral Β-amino Acid Derivatives by Mannich-type Reactions of Chiral N-sulfinyl Imidates with N-tosyl Aldimines.” Organic Letters 12 (9): 1904–1907.
APA
Colpaert, F., Mangelinckx, S., & De Kimpe, N. (2010). Asymmetric synthesis of new chiral β-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines. ORGANIC LETTERS, 12(9), 1904–1907.
Vancouver
1.
Colpaert F, Mangelinckx S, De Kimpe N. Asymmetric synthesis of new chiral β-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines. ORGANIC LETTERS. 2010;12(9):1904–7.
MLA
Colpaert, Filip, Sven Mangelinckx, and Norbert De Kimpe. “Asymmetric Synthesis of New Chiral Β-amino Acid Derivatives by Mannich-type Reactions of Chiral N-sulfinyl Imidates with N-tosyl Aldimines.” ORGANIC LETTERS 12.9 (2010): 1904–1907. Print.
@article{944962,
  abstract     = {New chiral beta-(sulfonylamino)sulfinylimidates are synthesized in high overall yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of chiral N-tert-butanesulfinyl imidates with N-tosyl aldimines. Deprotection of the beta-(sulfonylamino)sulfinylimidates gave access to enantiopure imidate hydrochlorides in high yields, as useful intermediates for an easy transformation to new chiral beta-sulfonylamino amides upon simple heating in chloroform. Hydrolysis of the imidate hydrochlorides afforded the corresponding chiral beta-sulfonylamino esters with {\textrangle}98\% ee as new chiral beta-amino acid derivatives.},
  author       = {Colpaert, Filip and Mangelinckx, Sven and De Kimpe, Norbert},
  issn         = {1523-7060},
  journal      = {ORGANIC LETTERS},
  language     = {eng},
  number       = {9},
  pages        = {1904--1907},
  title        = {Asymmetric synthesis of new chiral \ensuremath{\beta}-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines},
  url          = {http://dx.doi.org/10.1021/ol100073y},
  volume       = {12},
  year         = {2010},
}

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