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ChemInform Abstract: Intramolecular Reaction of (γ-Alkoxyallyl)stannane with Aldehyde: Origin of the Stereoselectivities.

✍ Scribed by I. KADOTA; M. KAWADA; V. GEVORGYAN; Y. YAMAMOTO

Publisher
John Wiley and Sons
Year
2010
Weight
42 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Intramolecular Reaction of (γ-Alkoxyallyl)stannane with Aldehyde: Origin of the Stereoselectivities. -The Lewis acid-mediated cyclization of acyclic (γ-alkoxyallyl)stannane aldehydes leads to trans-substituted cyclic ethers predominantly or exclusively, irrespective of the geometry of the double bond and ring size of cyclic ethers. Protic acid-induced reactions of the derivatives (I), (IV), (IX), and (XI) also give the trans cyclic ethers, regardless of the double bond geometry, whereas protic acid as well as thermal-induced reactions of the stannanes (V) and (VIII) strongly depend on the double bond geometry. Unexpectedly, thermal cyclization of (IX) and (XI) is inefficient. Reaction mechanisms are discussed. -(KADOTA, I.;

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✍ I. KADOTA; S. SAYA; Y. YAMAMOTO 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB

Novel Route to the Synthesis of Hydroxylated Pyrrolidine Derivatives via the Intramolecular Reaction of γ-Aminoallylstannane with Aldehyde. Total Synthesis of (+)-Preussin. -Contrary to Lewis acid mediated reaction, the thermal cyclization of γ-amino allylstannane (I) having an aldehyde group gives