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:

B. Saito, G. C. Fu, J. Am. Chem. Soc., 2007, 129, 9602–9603.

(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.)

For asymmetric hydroboration another bulky group is used - Ipc: enter image description here

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?

EDIT: I've found this reaction sequence in Carey, Sundberg Advanced Org. Chem: enter image description here

The product could be used for a Suzuki couping, but the question whether the stereochemical information is lost during coupling remains open.

  • $\begingroup$ Is this the sort of thing ncbi.nlm.nih.gov/pmc/articles/PMC2929007 your asking about? $\endgroup$ – user1945827 Aug 23 '16 at 14:45
  • $\begingroup$ That article explains the enantioselectivity in the case of chiral halide, I am asking about chiral organoboranes. $\endgroup$ – RBW Aug 23 '16 at 17:50
  • $\begingroup$ As of 2010, when I wrote my thesis and papers on the alkyl-alkyl couplings, I do not believe there were any asymmetric variants using a chiral borane. $\endgroup$ – Zhe Jun 21 '17 at 21:07
  • $\begingroup$ I found this reference, but I don't have access to read it: pubs.acs.org/doi/abs/10.1021/jo201263r Amusingly, I worked with Liz also when we were both in the Jacobsen lab. $\endgroup$ – Zhe Jun 22 '17 at 3:16
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    $\begingroup$ Maybe that's not surprising. The transmetallation and reductive elimination steps are most likely concerted and not reversible. $\endgroup$ – Zhe Jun 22 '17 at 14:18

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