publication . Article . Other literature type . 2013

Origins of 1,6-stereoinduction in torquoselective 6π electrocyclizations.

Ashay Patel; Gregg A Barcan; Ohyun Kwon; K N Houk;
Open Access
  • Published: 18 Mar 2013 Journal: Journal of the American Chemical Society, volume 135, pages 4,878-4,883 (issn: 0002-7863, eissn: 1520-5126, Copyright policy)
  • Publisher: American Chemical Society (ACS)
A novel stereoselective electrocyclization developed for the total synthesis of reserpine has been explored by both experiment and theory. A stereocenter six atoms away from the newly forming chiral center is responsible for the diastereoselectivity of the ring closure. This stereogenic center, lying at the junction of two six-membered rings, defines the conformation of the substrates’ fused ring skeleton that ultimately distinguishes between the two allowed, disrotatory triene geometries at the transition state. The presence of allylic strain in the disfavored transition state results in a torquoselective ring closure (dr up to 15.7:1).
free text keywords: Colloid and Surface Chemistry, Biochemistry, General Chemistry, Catalysis, Stereoselectivity, Allylic strain, Chemistry, Chirality (chemistry), Organic chemistry, Conrotatory and disrotatory, Total synthesis, Stereochemistry, Stereoisomerism, Stereocenter, Article
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