Synthesis of Optically Pure 2-Aziridinemethanols : Versatile Synthetic Building Blocks

Synthesis of three cis-trans pairs of N-sulfonylated-2-aziridinemethanols starting from (S)-threonine, (R)-allothreonine, a chiral 2-amino alcohol, or enantiomerically enriched 2, 3-epoxy alcohols is described. A synthetic route to N-tosyl- and N-mesyl-2-aziridinemethanols from (R)- and (S)-serines...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 42; no. 11; pp. 2241 - 2250
Main Authors FUJII, Nobutaka, NAKAI, Kazuo, HABASHITA, Hiromu, HOTTA, Yuka, TAMAMURA, Hirokazu, OTAKA, Akira, IBUKA, Toshiro
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 1994
Pharmaceutical Soc Japan
Maruzen
Subjects
(R)-allothreonine
(R)-serine
(S)-serine
(S)-threonine
2, 3-epoxy alcohol
2-aziridinemethanol
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Life Sciences & Biomedicine
Organic chemistry
Pharmacology & Pharmacy
Physical Sciences
Preparations and properties
Science & Technology
2-AZIRIDINEMETHANOL
(R)-ALLOTHREONINE
RESOLUTION
(S)-SERINE
ENANTIODIVERGENT SYNTHESIS
(R)-SERINE
STRATEGIES
2,3-EPOXY ALCOHOLS
(S)-THREONINE
AMINO-ACIDS
ESTERS
MITOMYCINS
2,3-EPOXY ALCOHOL
CHIRAL AZIRIDINES
NUCLEOPHILIC-ATTACK
DERIVATIVES
Stereoselectivity
α-Aminoacid
Threonine
Nitrogen heterocycle
Serine
Epoxide
Three membered ring
Alcohol
Chemical synthesis
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Summary:Synthesis of three cis-trans pairs of N-sulfonylated-2-aziridinemethanols starting from (S)-threonine, (R)-allothreonine, a chiral 2-amino alcohol, or enantiomerically enriched 2, 3-epoxy alcohols is described. A synthetic route to N-tosyl- and N-mesyl-2-aziridinemethanols from (R)- and (S)-serines is also presented.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.42.2241