Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates.
Propargylic pivalates with electronically unbiased internal alkynes are selectively transformed into (1Z,3E)-2-pivaloxy-1,3-dienes containing various functionalities. The unusual selectivity of 1,2-acyloxy migration over the structurally preferred 3,3-rearrangement is realized. This reaction is highly stereoselective and offers rapid access to dienes for one-pot intra-/intermolecular Diels-Alder reactions either under thermal conditions or with Lewis acid catalysis.
Li
Guotao
G
Department of Chemistry/216, University of Nevada, Reno, 1664 North Virginia Street, Reno, Nevada 89557, USA.
Zhang
Guozhu
G
Zhang
Liming
L
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D050607:Organogold Compounds / Q000737:chemistry*; D010421:Pentanoic Acids / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D000480:Alkynes; D050607:Organogold Compounds; D010421:Pentanoic Acids; C005566:pivalic acid