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Synthesis of optically active α-sulfinylacetaldehyde

✍ Scribed by P. Pflieger; C. Mioskowski; J.P. Salaun; D. Weissbart; F. Durst

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
197 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Recently several groups have utilized chiral P-hydroxysulfoxides 2 lm4, via the corresponding P-ketosulfoxides 3, for the synthesis of optically active epoxides 4 and secondary alcohols 5. Both antipodes of the epoxide and alcohol are accessible from the same P-ketosulfoxide B by stereoselective reduction of the keto fonctionality (scheme 1).

Unfortunately, to vary the substituent R, it is necessary to synthesize the starting P-ketosulfoxide 3 in each case. We felt it would be advantageous to prepare a-sulfinylacetaldebyde 1 as a versatile reagent to which a wide range of nucleophiles could be added selectively to either face depending on the organometallic used, thus providing direct access to a variety of /3-hydroxysulfoxides 2.

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Convenient synthesis of optically active
Convenient synthesis of optically active α-hydroxyphosphinic acids
✍ Juexiao Cai; Zhenghong Zhou; Guofeng Zhao; Chuchi Tang 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 93 KB

## Abstract The reaction of O‐menthyl phenylphosphonite **__1__** with aromatic aldehydes in the presence of Me~3~SiCl provided the O‐menthyl α‐hydroxyphosphinates **__2__**. Acidic hydrolysis of **__2__** gave the corresponding α‐hydroxyphosphinic acids **__3__**. The (+)‐enantiomer of **__3a__**