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On the preparation of optically active secondary alcohols from a 1,3-dioxan-4-one: Substitution with organocopper reagents

✍ Scribed by Stuart L. Schreiber; Jeff Reagan

Book ID
104218768
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
285 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Organocopper reagents react with a chiral nonracemic 1,3-dioxan-4-one to afford substitution products with high diastereoselectivity.

After treatment of the adducts with potassium t-butoxide, optically active secondary alcohols are obtained. Recently a new chiral, nonracemic acetal for use in the formation of optically active secondary alcohols was described by Seebach et al. (eq 1J.I Several features of the 1,3-dioxan-4-one functional group

were outlined that suggested these chiral auxiliaries may be preferred to related acetals that have seen widespread use in organic synthesis.2-4

📜 SIMILAR VOLUMES

Application of Sharpless asymmetric epox
Application of Sharpless asymmetric epoxidation on the preparation of the optically active flavours 3-methylthiohexanal and 5(6)-butyl-1,4-dioxan-2-one
✍ Hong-yu Tian; Bao-guo Sun; Li-wei Tang; Hong-lin Ye 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 207 KB

## Abstract Optically active 2,3‐epoxyhexanol obtained from Sharpless asymmetric epoxidation (AE) was regioselectively reduced to 1,3‐hexandiol or 1,2‐hexandiol. 1,3‐Hexandiol was converted to 3‐mesyloxyhexyl acetate. The following reaction with CH~3~SK gave 3‐methylthiohexanol, which was oxidized

Nucleophilic substitution at the acetali
Nucleophilic substitution at the acetalic center of mandelate 1,3-dioxolan-4-ones using magnesio-copper reagents: Application to the synthesis of chiral secondary alcohols.
✍ Bertrand Heckmann; Charles Mioskowski; Jurong Yu; J.R. Falck 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 222 KB

## Ethereal magnesia-copper reagents, in contrast to lithio-copper reagents, add stereoselectively to man&lie acid derived 1,3-dioxolawl-ones to dord optically active secondary alcohol &er removal of the chiral auxiliary. 1,3-Dioxan-4-ones' and 1,3-dioxolan-4-one& e.g., (1) and (2). respectively.