Premium
One Stone for Three Birds‐Rhodium‐Catalyzed Highly Diastereoselective Intramolecular [4+2] Cycloaddition of Optically Active Allene‐1,3‐dienes
Author(s) -
Han Yulin,
Qin Anni,
Ma Shengming
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900023
Subject(s) - allene , chemistry , intramolecular force , cycloaddition , enantiomer , rhodium , chirality (physics) , axial chirality , optically active , catalysis , bicyclic molecule , stereochemistry , absolute configuration , enantioselective synthesis , organic chemistry , physics , nambu–jona lasinio model , quark , chiral symmetry breaking , quantum mechanics
Summary of main observation and conclusion RhCl(PPh 3 ) 3 ‐catalyzed [4+2] intramolecular cycloaddition of optically active axially chiral allene‐dienes afforded cis ‐fused [3.4.0]‐bicyclic products with three chiral centers in good yields with an excellent chemo‐ and diastereoselectivity. A pair of enantiomers of such products was generated highly selectively from both enantiomers of starting allene‐dienes, indicating that the axial chirality dictated the absolute configurations of the three in situ generated chiral centers with a very high efficiency of chirality transfer.