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9
. For selected reactions of Rh(II)-azavinyl carbenoids with alcohols, carboxylic acids, esters and/or ethers in
addition to references 4s-u, 5a, 5s, 5aa, 5ad, 5af, 5ah, and 6-8, see: (a) Miura, T.; Tanaka, T.; Biyajima, T.; Yada, A.;
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Z.; Lee, S. ACS Catal. 2016, 6, 4914.
(
1
9
0. For selected reactions of N-(2-alkoxyvinyl)sulfonamides in addition to references 4r, 5aa, 5ad, 5ah, 6b, 8, and
a-d, see: (a) Alford, J. S.; Davies, H. M. L. J. Am. Chem. Soc. 2014, 136, 10266; (b) Miura, T.; Tanaka, T.;
Matsumoto, K.; Murakami, M. Chem. Eur. J. 2014, 20, 16078; for reactions of the structurally similar N-(2-
siloxyvinyl)sulfonamide, see: (c) Miura, T.; Nakamuro, T.; Kiraga, K.; Murakami, M. Chem. Commun. 2014, 50,
1
1
0474.
1. In a test reaction, a small sample of 13 was cleanly converted to 12 in 1:4 H
2
SO
4
/1,4-dioxane as evidenced by
1
TLC, H NMR, and ESI-MS.
1
2. No observable quantities of ketal 13 was produced when furan 12 was subjected to 2.0 eq of alkynol 10, 0.1 eq
CuTC, and 0.01 eq Rh (OAc) in refluxing CHCl for 1.5h.
2
4
3
1
3. 14a is commercially available. For the synthesis of 14b via addition of phenylmagnesium bromide to 2-
ethynylbenzaldehyde, see: Chem. Eur. J. 2010, 16, 7889; alkynol 14c was prepared in 35% yield by using iso-propyl
magnesium chloride in a similar manner.
1
3