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. Author manuscript; available in PMC: 2023 Jan 19.
Published in final edited form as: ACS Catal. 2022 Jun 7;12(12):7377–7385. doi: 10.1021/acscatal.2c01232

Table 5.

Solvent Effect on the Cyclization of Dialkyl-Substituted Alkene 3a,bcd

graphic file with name nihms-1864304-t0013.jpg
Entry Substrate Conditions Selectivity (a:b) Product e.r.
1 graphic file with name nihms-1864304-t0014.jpg HFIP 1.3:1 anti-21a + trans-21b (6)c = 98:2
(5) = 98:2
2 CH2Cl2
MsOH (0.4 equiv)		 1:2 anti-21a + trans-21b (6)c = 98:2
(5) = 98:2
3 graphic file with name nihms-1864304-t0015.jpg HFIP >20:1 syn-21a + cis-21b 71:29d
4 CH2Cl2
MsOH (0.4 equiv)		 >20:1 syn-21a + cis-21b 67:33d
a

All reactions performed on a 0.10 mmol scale.

b

Enantiomeric ratio determined by CSP-HPLC analysis.

c

Enantiomeric ratio determined on corresponding sulfone.

d

Enantiomeric ratio determined for syn-21a.