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Remarkable Efficiency in the Catalytic Asymmetric Epoxidation of (E)-3-Trimethylsilyl-2-propen-1-ol

Yuichi Kobayashi, Takayori Ito, Isao Yamakawa, Hirokazu Urabe, Fumie Sato

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Abstract

All articles of this category The Sharpless epoxidation of ( E )-3-trimethylsilyl-2-propen-1-ol ( 3 ) affords the corresponding epoxide 4 [(2 S ,3 S )-2, 3-epoxy-3-trimethylsilylpropan-1-ol] in 99% enantiomeric excess in the presence of only 3 mol% of the catalyst (Ti(O i -Pr) 4 /L-(+)-diisopropyl tartrate). The epoxide 4 is further converted into various ( S )-glycidol [( S )-2, 3-epoxypropan-1-ol] derivatives with retention of optical purity.

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What this paper is about

All articles of this category The Sharpless epoxidation of ( E )-3-trimethylsilyl-2-propen-1-ol ( 3 ) affords the corresponding epoxide 4 [(2 S ,3 S )-2, 3-epoxy-3-trimethylsilylpropan-1-ol] in 99% enantiomeric excess in the presence of only 3 mol% of the catalyst (Ti(O i -Pr) 4 /L-(+)-diisopropyl tartrate). The epoxide 4 is further converted into various ( S )-glycidol [( S )-2, 3-epoxypropan-1-ol] derivatives with retention of optical purity.

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Available abstract

All articles of this category The Sharpless epoxidation of ( E )-3-trimethylsilyl-2-propen-1-ol ( 3 ) affords the corresponding epoxide 4 [(2 S ,3 S )-2, 3-epoxy-3-trimethylsilylpropan-1-ol] in 99% enantiomeric excess in the presence of only 3 mol% of the catalyst (Ti(O i -Pr) 4 /L-(+)-diisopropyl tartrate). The epoxide 4 is further converted into various ( S )-glycidol [( S )-2, 3-epoxypropan-1-ol] derivatives with retention of optical purity.

Key concepts: Chemistry, Epoxide, Glycidol, Trimethylsilyl, Sharpless epoxidation, Catalysis, Enantiomer, Tartrate

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