Table 2.

Scope of the rhodium-catalyzed allylic etherification with the copper(I) alkenyl alkoxides 2 followed by ring-closing metathesis.^[a],^[b]

Entry	Config. of 2	n	d.r.[c]	Yield of addition product [%][d]	Cyclic ether	Yield [%][d]
1	R	0	53:1	74	5a	94
2	S	0	1:50	78	ent-6a	99
3	R	1	23:1	77	5b	85
4	S	1	1:23	76	ent-6b	98
5	R	2	27:1	77	5c	85
6	S	2	1:26	77	ent-6c	93
7	R	3	29:1	77	5d	73[e]
8	S	3	1:39	77	ent-6d	82[e]

^[a]All allylic etherification reactions (0.25 mmol) were carried out with 10 mol% of the catalyst in tetrahydrofuran with 1.9 equivalents of the copper alkoxide. The regioselectivity (2°/1°) observed for the addition of the copper alkoxide was ≥99:1 in all cases. (Authentic standards were prepared independently by using copper cyanide as an additive.)

^[b]All ring-closing metathesis reactions were carried out on a 0.1-mmol scale with 5-10 mol% of the Grubbs catalyst in dichloromethane (0.1M).

^[c]Ratios of regio- and diastereoisomers were determined by capillary GLC on aliquots of the crude reaction mixture.

^[d]Yields of the isolated products.

^[e]The Grubbs N-heterocyclic carbene catalyst (0.001M) was used at reflux.