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Asymmetric Aldol Reaction of α‐Acetoxyimino Aldehydes and its Application in the Synthesis of Substituted 1,2‐Oxazine Derivatives
Author(s) -
Yasui Yusuke,
Ogata Kento,
Sato Itaru,
Hayashi Yujiro
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400294
Subject(s) - aldol reaction , chemistry , nucleophile , yield (engineering) , aldehyde , organic chemistry , enantioselective synthesis , catalysis , materials science , metallurgy
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 via sequential reactions such as deacetylation, oxy‐Michael reaction and reduction.