Asymmetric Induction With Chiral Carbon-Bonding Donors.

Carbon bonding has recently been introduced as a new tool in organic synthesis. Yet, it remains unclear whether this unique weak interaction can induce chirality or not. Herein, we report the synthesis of chiral carbon-bonding donors, and present the proof-of-concept study on asymmetric induction using this noncovalent force. Employing the oxa-Pictet-Spengler reaction as a benchmark, the experimental results demonstrate that chiral carbon-bonding donors can exert asymmetric induction over oxocarbenium ion intermediates. While the enantioselectivity in such a very first attempt is modest, it unequivocally validates carbon bonding as a feasible method for asymmetric induction, paving the way for its future development in more efficient asymmetric synthesis.