Premium
Enantioselective Cyclopropanation with TADDOL‐Derived Phosphate Ligands
Author(s) -
Voituriez Arnaud,
Charette André B.
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600351
Subject(s) - cyclopropanation , chemistry , enantioselective synthesis , phosphate , organic chemistry , combinatorial chemistry , catalysis
The synthesis of new chiral TADDOL‐derived phosphate ligands is described. The ligands were efficiently synthesized on a multi‐gram scale in three steps starting from the readily available corresponding TADDOL and were fully characterized. An X‐ray structure was obtained and compared to known BINOL‐phosphates. Their use in the asymmetric Simmons–Smith cyclopropanation of both functionalized and unfunctionalized olefins gave the desired cyclopropanes in good yields and good to moderate enantioselectivities.