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Enantioselective Cobalt‐Catalyzed [6+2] Cycloadditions of Cycloheptatriene with Alkynes
Author(s) -
Toselli Nicolas,
Martin David,
Achard Mathieu,
Tenaglia Alphonse,
Bürgi Thomas,
Buono Gerard
Publication year - 2008
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.200700424
Subject(s) - chemistry , enantioselective synthesis , cycloheptatriene , cobalt , trimethylsilyl , catalysis , circular dichroism , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry
The enantioselective cobalt‐catalyzed [6+2] cycloadditions of cycloheptatriene 1 with alkynes 2 is reported. Chiral phosphoramidites based on 3,3′‐disubstituted ( R )‐BINOL appeared to be efficient ligands, affording the corresponding cycloadducts with good yields and up to 92 % ee . A vibrational circular dichroism study afforded the absolute configuration of new chiral (+)‐(1 S ,6 R )‐7‐phenyl[4.2.1]bicyclo‐ nonatriene 3a and (−)‐(1 S ,6 R )‐7‐trimethylsilyl[4.2.1]bicyclononatriene 3c .