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Highly chemoselective Pummerer reactions of sulfinyldiacetic acid derivative

✍ Scribed by Yoshimitsu Nagao; Satoshi Miyamoto; Kazuhiko Hayashi; Ado Mihira; Shigeki Sano

Book ID
104250478
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
129 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Sulfinyldiacetic acid amide ester rac-1 was efficiently synthesized starting from thiodiacetic acid 4. Treatment of rac-1 with Ac 2 O and TMSOTf in CH 2 Cl 2 at -40Β°C gave chemoselectively amide site a-acetoxy sulfide rac-2 in a ratio (91:9) of rac-2 and rac-3 and in a 90% total yield. Similar treatment of 1 with Ac 2 O and TMSOTf in DMF at room temperature furnished ester site a-acetoxy sulfide rac-3 in a highly chemoselective manner (rac-2:rac-3=3:97) and in a 92% total yield.

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