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A simple and convenient synthesis of β-amino alcohol chiral auxiliaries based on limonene oxide

✍ Scribed by Will Chrisman; Jason N Camara; Kim Marcellini; Bakthan Singaram; Christian T Goralski; Dennis L Hasha; Philip R Rudolf; Lawrence W Nicholson; Karen K Borodychuk

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
66 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

A series of chiral b-amino alcohols was prepared by the reaction of secondary amines with a 1:1 mixture of cis-and trans-limonene oxide in the presence of water as a catalyst. The b-amino alcohol obtained was derived from the trans-limonene oxide, and the unreacted cis-limonene oxide was recovered from the reaction mixture. The b-amino alcohols are useful chiral auxiliaries for the addition of diethylzinc to benzaldehyde.

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A convenient synthesis of piperidine-bas
A convenient synthesis of piperidine-based β-amino alcohols from l-Phe and highly enantioselective addition of diethyl zinc to aldehydes
✍ Chao-shan Da; Zhi-jian Han; Ming Ni; Fan Yang; Da-xue Liu; Yi-feng Zhou; Rui Wan 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 172 KB

b-Amino alcohols 4a-e were easily prepared from L-phenylalanine in three simple straightforward steps. The key intermediate compound (S)-3 was achieved in high yield (up to 92%) with glutaraldehyde and NaBH 4 /H 2 SO 4 in THF at room temperature. These five ligands were applied to catalyze enantiose