TY - JOUR
T1 - Boronate Ester Bullvalenes
AU - Patel, Harshal D.
AU - Tran, Thanh-Huyen
AU - Sumby, Christopher J.
AU - Pašteka, Lukáš F.
AU - Fallon, Thomas
PY - 2020/2/26
Y1 - 2020/2/26
N2 - Boronate ester bullvalenes are now accessible in two to four operationally simple steps. This unlocks late-stage diversification through Suzuki cross-coupling reactions to give mono-, di-, and trisubstituted bullvalenes. Moreover, a linchpin strategy enables preprogrammed installation of two different substituents. Analysis of solution phase isomer distributions and single-crystal X-ray structures reveals that isomer preference in the crystal lattice is due to general shape selectivity.
AB - Boronate ester bullvalenes are now accessible in two to four operationally simple steps. This unlocks late-stage diversification through Suzuki cross-coupling reactions to give mono-, di-, and trisubstituted bullvalenes. Moreover, a linchpin strategy enables preprogrammed installation of two different substituents. Analysis of solution phase isomer distributions and single-crystal X-ray structures reveals that isomer preference in the crystal lattice is due to general shape selectivity.
KW - Boronate ester bullvalenes
KW - Suzuki cross-coupling reactions
KW - Isomer
UR - http://www.scopus.com/inward/record.url?scp=85081336200&partnerID=8YFLogxK
UR - http://purl.org/au-research/grants/ARC/LE0989336
U2 - 10.1021/jacs.9b12930
DO - 10.1021/jacs.9b12930
M3 - Article
C2 - 32041409
AN - SCOPUS:85081336200
SN - 0002-7863
VL - 142
SP - 3680
EP - 3685
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 8
ER -