TY - JOUR
T1 - One-Pot, Tandem Wittig Hydrogenation
T2 - Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope
AU - Devlin, Rory
AU - Jones, David J.
AU - Mcglacken, Gerard P.
N1 - Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/7/2
Y1 - 2020/7/2
N2 - A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.
AB - A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.
UR - https://www.scopus.com/pages/publications/85087528411
U2 - 10.1021/acs.orglett.0c01874
DO - 10.1021/acs.orglett.0c01874
M3 - Article
C2 - 32574057
AN - SCOPUS:85087528411
SN - 1523-7060
VL - 22
SP - 5223
EP - 5228
JO - Organic Letters
JF - Organic Letters
IS - 13
ER -