NDLI: Asymmetric Synthesis of 3-Substituted Hexahydro-3H-isochromenes via an Organocatalytic Triple Cascade/Yb-Catalyzed Hetero-Diels-Alder Sequence

Content Provider	Scilit
Author	Enders, Dieter Erdmann, Nico Atodiresei, Iuliana
Copyright Year	2012
Description	An efficient two-step asymmetric synthesis of highly substituted 3-alkoxy-hexahydro-3H-isochromenes and 3-sulfenylated hexahydro-3H-isochromenes is described. The procedure involves an organocatalytic triple cascade reaction, followed by an intermolecular $[Yb(fod)_{3}$]-catalyzed inverse-electron-demand hetero-Diels–Alder reaction. Using this strategy, a total of six stereogenic centers are obtained with excellent diastereoselectivities and virtually complete enantioselectivities (>95:5 dr, >99% ee).
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0031-1290374.pdf
Ending Page	2113
Page Count	7
Starting Page	2107
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-0031-1290374
Journal	Synthesis
Issue Number	13
Volume Number	44
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2012-06-04
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry Diels–alder Reaction
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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Asymmetric Synthesis of 3-Substituted Hexahydro-3H-isochromenes via an Organocatalytic Triple Cascade/Yb-Catalyzed Hetero-Diels-Alder Sequence