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. Author manuscript; available in PMC: 2017 Jul 1.
Published in final edited form as: Org Lett. 2016 Jun 13;18(13):3214–3217. doi: 10.1021/acs.orglett.6b01435

Table 1.

Enantioselective Oxocarbenium Alkylation Enabled by Designed Catalyst Me-1.a

graphic file with name nihms826608t1.jpg

entry nucleophile time (h) cat. conv
(%)b
ee
(%)
1 3a 4 1 66 92c
2 Me-1 >95 97c
3 3b 1 1 81 85d
4 Me-1 91 91d
5 3c 24 1 82 88d
6 Me-1 >95 96d
a

Reactions were run on 0.2 or 0.3 mmol scale and quenched after the designated time with 0.5 M NaOMe in MeOH. See footnote 12.

b

Conversion was determined from the relative integration of the 1H NMR resonances of the product and quenched α-methoxyisochroman.

c

Determined by CSP-GC.

d

Determined by CSP-HPLC.