Sequential Catalytic Asymmetric Allylic Transfer Reaction: Enantioselective and Diastereoselective Construction of Tetrahydropyran Units

Useful tetrahydropyran units such as 3 can be prepared with high diastereoselectivity (d.r.>30:1). A key step is the catalytic asymmetric allyl‐transfer reaction from 1 to achiral aldehydes catalyzed by [{(R)‐binol}TiIV{OCH(CF3)2}2] to give 2 (90–97 % ee). A second allyl‐transfer reaction from 2...

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Veröffentlicht in:	Angewandte Chemie International Edition 2002-01, Vol.41 (1), p.161-163
Hauptverfasser:	Yu, Chan-Mo, Lee, Jae-Young, So, Byungran, Hong, Junghyun
Format:	Artikel
Sprache:	eng
Schlagworte:	aldehydes asymmetric catalysis chirality Lewis acids titanium
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	Useful tetrahydropyran units such as 3 can be prepared with high diastereoselectivity (d.r.>30:1). A key step is the catalytic asymmetric allyl‐transfer reaction from 1 to achiral aldehydes catalyzed by [{(R)‐binol}TiIV{OCH(CF3)2}2] to give 2 (90–97 % ee). A second allyl‐transfer reaction from 2 to a carbonyl compound leads to 3. binol=2,2′‐binaphthol.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/1521-3773(20020104)41:1<161::AID-ANIE161>3.0.CO;2-N