ArticleThe Journal of organic chemistry2013
Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by Prins cyclization.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.Organic letters · 2013Article
- Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis.Tetrahedron · 2013Article
- Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues.Synthesis · 2013Article
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4 authors.
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Abstract
The Prins cyclization of syn-β-hydroxy allylsilanes and aldehydes gives cis-2,6-disubstituted 4-alkylidenetetrahydropyrans as sole products in excellent yields regardless of the aldehyde (R″) or syn-β-hydroxy allylsilane substituent (R') used. By reversing the R″ and R' groups, complementary exocyclic stereocontrol can be achieved. When the anti-β-hydroxy allylsilanes are used, the Prins cyclization gives predominantly cis-2,6-disubstituted 4-alkylidenetetrahydropyrans, now with the opposite olefin geometry in excellent yield. The proposed reaction mechanism and the observed stereoselectivity for these processes are supported by DFT calculations.
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