. Author manuscript; available in PMC: 2019 Nov 7.

Published in final edited form as: J Am Chem Soc. 2018 Oct 26;140(44):14836–14843. doi: 10.1021/jacs.8b08605

Table 3.

Alkyl Chloride Scope of Ti-Catalyzed Alkylation^a

All reactions were conducted on 0.1 mmol scale with isolated yields reported.

With 2 equiv of alkene.

In the major product, 2 is added trans to Ph.

With 15 mol % Ti catalyst and 5 equiv of 2.

Cis-fused bicycle was formed as the observable stereoisomer.

Using alkene 14 instead of 2.

Using 14 as the limiting agent with 4 equiv of R–Cl.

With 20 mol % Ti catalyst for 72 h.

ⁱ

Using 3 equiv of Zn and Et₃N⋅HCl.

Using 14 as the limiting agent with 2 equiv of R–Cl.

Only one stereoisomer was isolated; the stereochemistry at C2 is tentatively assigned as exo using 2D NMR.

Using 4 equiv of 2.

The configuration of C1 in the major product is S.

ⁿ

1 mmol scale with 20 mol % Ti catalyst.

Using 20 mol% Ti catalyst, 3 equiv Zn, Et₃N⋅HCl, and 2; relative stereochemistry of the major product could not be determined.

The configuration of C3 in the major product is S.