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Synthesis of Enantiopure Tertiary Skipped Diynes via One-Pot Desymmetrizing TMS-Cleavage
- Source :
- Organic Letters, Organic Letters, American Chemical Society, 2012, 14 (15), pp.3974--3977. ⟨10.1021/ol3017462⟩, Organic Letters, 2012, 14 (15), pp.3974--3977. ⟨10.1021/ol3017462⟩
- Publication Year :
- 2012
- Publisher :
- American Chemical Society (ACS), 2012.
-
Abstract
- International audience; Enantiopure tetrasubstituted skipped diynes were readily synthesized from N-protected amino esters upon addition of lithium TMS-acetylide which was found to be desymmetrizing through one-pot selective TMS-cleavage. The deprotection of the TMS group was realized through a one-pot silicon atom attack by the liberated methoxide, which was diastereoselective due to a conformational favorable chelate.
- Subjects :
- Amino esters
010405 organic chemistry
Chemistry
Stereochemistry
Organic Chemistry
Methoxide
010402 general chemistry
Cleavage (embryo)
01 natural sciences
Biochemistry
0104 chemical sciences
chemistry.chemical_compound
Enantiopure drug
[CHIM]Chemical Sciences
Chelation
Physical and Theoretical Chemistry
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 14
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....aa2f4cc28892760178f28433b88ba087
- Full Text :
- https://doi.org/10.1021/ol3017462