## Abstract Using the readily accessible chiral auxiliaries **1**–**3** the sulfonamide‐shielded __O__‐silylated esters **5** underwent π‐face‐selective α‐acetoxylation on successive treatment with Pb(OAc)~4~ and NEt~3~ HF to give after recrystallization α‐acetoxy ester **6** in 55–67% yields and i
Efficient Conversion of Esters to α-Trimethylsilylketones. Preliminary communication
✍ Scribed by Martin Demuth
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- German
- Weight
- 146 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Secondary and tertiary carboxylic methyl or ethyl esters (2a‐c) were converted with trimethylslylmethyllithium (3a‐c) in high yields. Under identical reaction conditions the primary esters 2d,e gave 3d, e in lower yields. Since the trimethylsilyl (TMS) group α to a ketone is known to undergo facile elimination under a variety of reaction conditions, the method also constitutes a highly versatile ester to methylketone sequence.
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## Abstract Penicillin G (**1**, R CH~2~Ph) was converted to cephaloram‐ and 6‐epicephaloram lactones **11** and **12** respectively by the initial replacement of thiazolidine part of penicillin by the mercaptan **9** followed by intramolecular cyclization and subsequent introduction of double bo
## Abstract For Abstract see ChemInform Abstract in Full Text.
## Abstract For Abstract see ChemInform Abstract in Full Text.
## Abstract For Abstract see ChemInform Abstract in Full Text.