Tetrahedron p. 5177 - 5188 (1993)
Update date:2022-09-26
Topics:
Grigg
Santhakumar
Sridharan
Thornton-Pett
Bridge
The synthesis of (R,R)-crinan from (S)-1-cyclohexenylethan-1-ol is described. The key palladium catalysed step involves a regiospecific 6-exo trig cyclisation which proceeds with 20:1 stereoselectivity for the trans-ring junction over the cis-ring fusion. The ring junction stereochemistry is sensitive to solvent, phosphine and small amounts of water.
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Doi:10.1021/jf00035a059
(1993)Doi:10.1016/S0957-4166(00)80127-5
(1993)Doi:10.1016/S0040-4020(97)00332-3
(1997)Doi:10.1021/ja00984a032
(1967)Doi:10.1021/ol403326z
(2014)Doi:10.1007/s11172-013-0148-4
(2013)
