185376-67-4Relevant academic research and scientific papers
Stereocontrol between remote atom centers in acyclic substrates. Anti addition of hydride to 1,5-, 1,6-, and 1,7-hydroxy ketones
Zhang, Han-Cheng,Harris, Bruce D.,Costanzo, Michael J.,Lawson, Edward C.,Maryanoff, Cynthia A.,Maryanoff, Bruce E.
, p. 7964 - 7981 (1998)
For conformationally unconstrained, acyclic organic compounds, the control of stereogenic centers at remote positions of a chain, that is, at a distance of four or more atom centers, remains a challenging problem in asymmetric synthesis. We report on our
High 1,6 diastereoselectivity in the hydride reduction of an acyclic ketone substrate via bicyclic chelation control
Zhang, Han-Cheng,Harris, Bruce D.,Maryanoff, Cynthia A.,Maryanoff, Bruce E.
, p. 7897 - 7900 (2007/10/03)
Reduction of acyclic ε-hydroxy ketone 3 with R-Alpine-Hydride in methylene chloride provided a strong preponderance of the anti diasteromer of 4 (anti:syn = 12:1). This impressive 1,6 stereoselectivity is attributed to bicyclic chelation control of hydride addition.
