Functionalized BINOL Derivatives as Ligands for Enantioselectively Catalyzed Aldol Additions: Highly Enantioselective Synthesis of Chiral β-Hydroxy Thioesters

Content Provider	Scilit
Author	Zimmer, Reinhold Schefzig, Luise Peritz, Anke Dekaris, Vjekoslav Reissig, Hans-Ulrich
Copyright Year	2004
Description	A series of 3,3′-disubstituted and 6,6′-disubstituted BINOL derivatives was synthesized and examined in typical titanium(IV) promoted aldol reactions. The model reaction of S-ketene silyl acetal 13 and aldehydes 12a and 12b revealed that 6,6′-dibromo-BINOL derivative (R)-6 is the ligand of choice for these transformations. Up to 97% yield with excellent enantioselectivity (ee > 97%) could be achieved. Scope and limitations were demonstrated using a series of aldehydes as substrates, which were generally transformed into their aldol adducts by the (R)-6/Ti(Oi-Pr)_{4}$ catalyst with good efficacy and high enantioselectivity.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2004-822364.pdf
Ending Page	1445
Page Count	7
Starting Page	1439
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-2004-822364
Journal	Synthesis
Issue Number	09
Volume Number	2004
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2004-05-10
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry Sonogashira Reaction Bissteroidal Ligand
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis