Radical migration-addition of N-tert-butanesulfinyl imines with organozinc reagents.

@article{Huang2013RadicalMO,
  title={Radical migration-addition of N-tert-butanesulfinyl imines with organozinc reagents.},
  author={W. Huang and Jian-Liang Ye and Wei Zheng and Han-Qing Dong and Bang-Guo Wei},
  journal={The Journal of organic chemistry},
  year={2013},
  volume={78 22},
  pages={
          11229-37
        }
}
A novel migration-addition sequence was discovered for the reaction of enantioenriched N-tert-butanesulfinyl iminoacetate 1a with functionalized benzylzinc bromide reagents, producing tert-leucine derivatives in excellent diastereoselectivity (dr 98:2). The absolute configurations of two new chiral centers were unambiguously assigned by chemical transformations and X-ray crystallography. In addition, the regio- and diastereoselectivities of this novel reaction were both explained through the… Expand
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