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Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.
- Source :
-
Organic letters [Org Lett] 2013 Nov 01; Vol. 15 (21), pp. 5436-9. Date of Electronic Publication: 2013 Oct 18. - Publication Year :
- 2013
-
Abstract
- An enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylate esters 3 via the reductive aldol reaction of ethyl allenecarboxylate (2) with 10-trimethylsilyl-9-borabicyclo[3.3.2]decane (1R) has been developed. Density functional theory calculations suggest that the allene hydroboration involves the 1,4-reduction of 2 with the 1R, leading directly to dienolborinate Z-(O)-8a.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 15
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 24138187
- Full Text :
- https://doi.org/10.1021/ol4025277