Rhodium Carbenoid Initiated O-H Insertion/Aldol/Oxy-Cope Cascade for the Stereoselective Synthesis of Functionalized Oxacycles

被引：17
作者：
Chinthapally, Kiran
Massaro, Nicholas P.
Sharma, Indrajeet [1 ]
机构：
[1] Univ Oklahoma, Dept Chem & Biochem, 101 Stephenson Pkwy, Norman, OK 73071 USA
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 24期
关键词：
ENANTIOSELECTIVE TOTAL-SYNTHESIS; RING EXPANSION; SUBSTITUTED TETRAHYDROFURANS; DIASTEREOSELECTIVE SYNTHESIS; CLAISEN REARRANGEMENT; NATURAL-PRODUCTS; CATALYSIS; ALCOHOLS; YLIDE;
D O I：
10.1021/acs.orglett.6b03229
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel diazo-cascade approach has been developed for the synthesis of nine-membered oxacycles utilizing readily accessible beta-hydroxy vinyl ketones and vinyl diazo esters. The Rh(II)-catalyzed cascade reaction begins with carbene O-H insertion followed by an intramolecular aldol cyclization to provide a substituted tetrahydrofuran intermediate that undergoes an oxy-Cope rearrangement to provide functionalized nine-membered oxacycles with complete stereoselectivity.
引用
收藏
页码：6340 / 6343
页数：4
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