Stereochemistry of palladium-mediated synthesis of PAMP-BH3: retention of configuration at P in formation of Pd-P and P-C bonds

Jillian R Moncarz; Tim J Brunker; David S Glueck; Roger D Sommer; Arnold L Rheingold

doi:10.1021/ja029404c

Stereochemistry of palladium-mediated synthesis of PAMP-BH3: retention of configuration at P in formation of Pd-P and P-C bonds

J Am Chem Soc. 2003 Feb 5;125(5):1180-1. doi: 10.1021/ja029404c.

Authors

Jillian R Moncarz¹, Tim J Brunker, David S Glueck, Roger D Sommer, Arnold L Rheingold

Affiliation

¹ 6128 Burke Laboratory, Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.

PMID: 12553815
DOI: 10.1021/ja029404c

Abstract

Treatment of Pd((S,S)-Chiraphos)(o-An)(I) (3, o-An = o-MeOC6H4) with either enantiomer of highly enantioenriched PH(Me)(Ph)(BH3) (1) gave the phosphido-borane complex Pd((S,S)-Chiraphos)(o-An)(P(Me)(Ph)(BH3)) (4) with retention of configuration at phosphorus, as shown by X-ray crystal structure determinations for both diastereomers of 4. Heating either diastereomer of 4 with diphenylacetylene gave Pd((S,S)-Chiraphos)(PhCCPh) (5) and P(o-An)(Me)(Ph)(BH3) (2) with retention of configuration at phosphorus.