9-BBN is applied for Suzuki coupling of a saturated alkyl chain with some alkenyl,alkynyl or even secondary alkyl halide like the modification attached:
(Saito, B.; Fu, G. C. Alkyl−Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature. J. Am. Chem. Soc. 2007, 129, 9602–9603. DOI:10.1021/ja074008l.)
Is there an asymmetric version of Suzuki coupling employing saturated groups where instead of 9-BBN, Icp or a similar chiral group would be used or would the stereochemical information be lost during transmetallation?
The product could be used for a Suzuki couping, but the question whether the stereochemical information is lost during coupling remains open.