Editing Enamine (section)

===Annulation===

Enamines chemistry has been implemented for the purposes of producing a one-pot enantioselective version of the [[Robinson annulation]]. The Robinson annulation, published by Robert Robinson in 1935, is a base-catalyzed reaction that combines a ketone and a [[methyl vinyl ketone]] (commonly abbreviated to MVK) to form a [[cyclohexenone]] fused ring system. This reaction may be catalyzed by [[proline]] to proceed through chiral enamine intermediates which allow for good stereoselectivity.<ref>{{cite journal|last1=List|first1=Benjamin|title=Proline-catalyzed asymmetric reactions|journal=Tetrahedron|date=2002|volume=58|issue=28|pages=5573–5590|doi=10.1016/s0040-4020(02)00516-1}}<!--|access-date=29 November 2014--></ref> This is important, in particular in the field of natural product synthesis, for example, for the synthesis of the [[Wieland–Miescher ketone|Wieland-Miescher ketone]] – a vital building block for more complex biologically active molecules.<ref>{{cite journal|last1=Bui|first1=Tommy|last2=Barbas|title=A proline-catalyzed asymmetric Robinson Annulation|journal=Tetrahedron Letters|date=2000|volume=41|issue=36|pages=6951–6954|doi=10.1016/s0040-4039(00)01180-1}}<!--|access-date=29 November 2014--></ref><ref>{{cite web|last1=Wiener|first1=Jake|title=Enantioselective Organic Catalysis:Non-MacMillan Approaches|url=https://www.princeton.edu/chemistry/macmillan/group-meetings/jjmw-orgcats.pdf|access-date=29 November 2014|archive-url=https://web.archive.org/web/20171026175935/http://www.princeton.edu/chemistry/macmillan/group-meetings/jjmw-orgcats.pdf|archive-date=26 October 2017|url-status=dead}}</ref>