Premium
Stereoselective Thermal Addition of R P and/or S P ‐Menthyl‐Deriving Secondary Phosphine Oxides to Active Alkynes, the Mechanism, Stereochemistry and Generation of P,C‐ Chirogenic Bis‐Phosphine Derivatives
Author(s) -
Yan BingXia,
Zheng HongXing,
Ye JingJing,
Qiu MaoRan,
Zhang Yu,
Zhao ChangQiu,
Li Qiang
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000079
Subject(s) - chemistry , stereoselectivity , phosphine , yield (engineering) , adduct , stereochemistry , medicinal chemistry , organic chemistry , catalysis , thermodynamics , physics
Abstract The additions of R P ‐ 1 or S P ‐ 1 to alkynyl esters stereo selectively afforded bis‐phosphinylated derivatives having up to four C‐ and P‐chirogenic centers. The stereochemistry was controlled by kinetic and thermodynamic processes at lower and higher temperature, respectively. At 100 °C, the bis‐adducts were obtained in up to 99% yield and >99 : 1 d.r.