Journal
ORGANIC LETTERS
Volume 25, Issue 1, Pages 5-10Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03335
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Rhodium(II) catalyst-controlled site- and stereo-selective carbene insertion into the allylic C(sp3)-H bond of allyl boronates is achieved. The chiral catalyst Rh2(S-TPPTTL)4 exhibits high fidelity and asymmetric induction, enabling diastereoselective and enantioselective C-C bond formation without interference from the allyl boronate functionality. The resulting functionalized allyl boronates are amenable to stereo-selective allylations, leading to products with control of stereochemistry at four contiguous stereogenic centers.
Rhodium(II) catalyst-controlled site-and stereo-selective carbene insertion into the distal allylic C(sp3)-H bond of allyl boronates is reported. The optimum chiral catalyst for this reaction is Rh2(S-TPPTTL)4. The fidelity and asymmetric induction of this catalytic transformation allows for a highly diastereoselective and enantioselective C-C bond formation without interference from the allyl boronate functionality. The resulting functionalized allyl boronates are susceptible to stereo-selective allylations, generating products with control of stereo-chemistry at four contiguous stereogenic centers.
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