Stereocontrol between Remote Atom Centers in Acyclic Substrates. Anti Addition of Hydride to 1, 5-, 1, 6-, and 1, 7-Hydroxy Ketones

…, MJ Costanzo, EC Lawson, CA Maryanoff…

Index: Zhang, Han-Cheng; Harris, Bruce D.; Costanzo, Michael J.; Lawson, Edward C.; Maryanoff, Cynthia A.; Maryanoff, Bruce E. Journal of Organic Chemistry, 1998 , vol. 63, # 22 p. 7964 - 7981

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Citation Number: 21

Abstract

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 studies of 1, 5, 1, 6, and 1, 7 diastereoselectivity in hydride reductions of acyclic hydroxy amino ketones and related compounds, which were sparked by our discovery of high 1, 5 diastereocontrol (> ...