NDLI: Asymmetric Synthesis of Highly Functionalized Cyclopentanes by a Rhodium- and Scandium-Catalyzed Five-Step Domino Sequence.

Content Provider	Semantic Scholar
Author	Parr, Brendan T. Li, Zhanjie Davies, Huw M. L.
Copyright Year	2011
Abstract	A domino sequence has been developed between vinyldiazoacetates and racemic allyl alcohols, involving five distinct steps. The sequence generates highly functionalized cyclopentanes with four new stereogenic centers as single diastereomers in 64-92% ee. The first step is a rhodium-catalyzed oxygen ylide formation, which is then followed by a [2,3]-sigmatropic rearrangement, an oxy-Cope rearrangement, a keto/enol tautomerization, and then finally a carbonyl ene reaction. With appropriate substrates, a further silyl deprotection and a 6-exo-trig cyclization can be added to the domino process.
Starting Page	2378
Ending Page	2382
Page Count	5
File Format	PDF HTM / HTML
DOI	10.1039/C1SC00434D
Alternate Webpage(s)	http://www.rsc.org/suppdata/sc/c1/c1sc00434d/c1sc00434d.pdf
PubMed reference number	22708053
Alternate Webpage(s)	https://doi.org/10.1039/C1SC00434D
Journal	Medline
Volume Number	2
Issue Number	12
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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