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. Author manuscript; available in PMC: 2010 Oct 8.
Published in final edited form as: Synlett. 2008 Feb 12;2008(3):363–366. doi: 10.1055/s-2008-1032053

Table 2.

Exploration of various electrophiles for the MAP reaction

Entry Electrophile Homoallylic Vinyl Ether Major Product Yield (%) dr (Br) eq:axa dr (OR)
1 graphic file with name nihms-111600-t0004.jpg 64 >95:5 1:1
2 graphic file with name nihms-111600-t0005.jpg 44 74:26 1:1
3 graphic file with name nihms-111600-t0006.jpg 71 89:11 7:3b,c
4 graphic file with name nihms-111600-t0007.jpg 61 95:5
5 graphic file with name nihms-111600-t0008.jpg 65 88:12 1:1
6 graphic file with name nihms-111600-t0009.jpg 36 82:18 1:1
7 graphic file with name nihms-111600-t0010.jpg 23 80:20 1:1
8 graphic file with name nihms-111600-t0011.jpg 90 92:8 7:3d
a

Ratios determined by integration of the crude 1H NMR spectra.

b

Ratio determined by HPLC analysis of the crude material.

c

Stereochemistry of the major isomer determined by removal of the chiral auxiliary and formation/analysis of both MPTA ester diastereomers.

d

Ratio of isolated products.