TY  - JOUR
AU  - Drennhaus, Till
AU  - Öhler, Laura
AU  - Djalali, Saveh
AU  - Höfmann, Svenja
AU  - Müller, Clemens
AU  - Pietruszka, Jörg
AU  - Worgull, Dennis
TI  - Enantioselective Ammonium Ylide Mediated One‐Pot Synthesis of Highly Substituted γ ‐Butyrolactones
JO  - Advanced synthesis & catalysis
VL  - 362
IS  - 12
SN  - 1615-4169
CY  - Weinheim
PB  - Wiley-VCH
M1  - FZJ-2020-03836
SP  - 2385 - 2396
PY  - 2020
AB  - An ammonium ylide mediated access towards trans‐β,γ‐disubstituted, all‐trans‐α,β,γ‐trisubstituted, and α,α,β,γ‐tetrasubstituted γ‐butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and α‐bromo carbonyl compounds, γ‐butyrolactones were obtained in yields between 32–99% with up to excellent diastereoselectivities (>95:5) via a DABCO‐mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R, 4R)‐β,γ‐disubstituted and (2R, 3R, 4R)‐α,β,γ‐trisubstituted γ‐butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration.
LB  - PUB:(DE-HGF)16
UR  - <Go to ISI:>//WOS:000540092500012
DO  - DOI:10.1002/adsc.202000039
UR  - https://juser.fz-juelich.de/record/885453
ER  -