Allenoate prenucleophiles: a triply diastereoselective approach to beta-hydroxy esters containing all-carbon alpha-quaternary centers
| Title | Allenoate prenucleophiles: a triply diastereoselective approach to beta-hydroxy esters containing all-carbon alpha-quaternary centers |
| Publication Type | Journal Article |
| Year of Publication | 2019 |
| Authors | Maki, SL, Maity, P, Dougherty, S, Johns, J, Lepore, SD |
| Journal | Organic Letters |
| Volume | 21 |
| Issue | 19 |
| Pagination | 7952-7955 |
| Date Published | OCT |
| Type of Article | Article |
| ISSN | 1523-7060 |
| Abstract | Allenyl esters activated by titanium(IV) underwent additions to a wide range of aldehydes in high regio- and diastereoselectivities leading to products containing an all carbon quaternary center bearing an alpha-vinyl group that was installed with high selectivity for the Z-geometry. An aldol product was also converted to an indanone offering a new route to this important compound class. Product triple diastereoselectivity has been rationalized using a concerted transition-state model. |
| DOI | 10.1021/acs.orglett.9b02930 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.555 |
Divison category:
Organic Chemistry