. Author manuscript; available in PMC: 2013 Feb 17.

Published in final edited form as: J Org Chem. 2012 Feb 8;77(4):1961–1973. doi: 10.1021/jo202553a

Table 2.

Catalytic Enantioselective Synthesis of 2-Vinyl-1,4-benzodioxanes (2) and 2-Vrnyl-2H-1,4-benzoxazines (3). graphic file with name nihms-356097-t0007.jpg

entry	X	R	imidate	catalyst (mol %)	time (h)	product	yield (%)^a	ee (%)^b
1	O	H	13	7 (0.5)	72	2	92	92 (S)^c
2	O	H	13	7 (2)	28	2	90	94 (S)^c
3	NTs	H	14	7 (2)	15	3	98	9S (S)^c
4	O	Me	15	ent-7 (5)	72	17	30	85^d
5	S	H	16	7 (5)	18	18	0	—

Mean yields after purification on silica gel of reactions performed in duplicate.

Determined by HPLC analysis using a enantioselective stationary phase (mean value of duplicate reactions).

Absolute configuration determined by comparison of optical rotation data with those reported in the literature.^6c,d

Absolute configuration was not established.