Asymmetric Aldol Reaction of α‐Acetoxyimino Aldehydes and its Application in the Synthesis of Substituted 1, 2‐Oxazine Derivatives. Issue 14 (10th September 2014)

• Record Type: Journal Article
• Authors: Yasui, Yusuke; Ogata, Kento; Sato, Itaru; Hayashi, Yujiro
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 14/15(2014)
• Page Start: 3106
• Page End: 3118
• Publication Date: 2014-09-10
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400294
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We have developed an asymmetric cross‐aldol reaction of α‐acetoxyimino aldehydes with aldehyde pro‐nucleophiles, catalyzed by proline, to afford γ‐acetoxyimino‐β‐hydroxy aldehydes in good yield with excellent enantioselectivity. The obtained aldol products have been successfully converted to 1, 2‐oxazines with four contiguous chiral centers in excellent diastereoselectivity in one‐pot <italic>via</italic> sequential reactions such as deacetylation, oxy‐Michael reaction and reduction.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh1fbrpbzv" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>