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Copper(I) mediated highly diastereoselective conjugate addition of grignard reagents to 2-silyloxycyclopentenecarboxylates
The conjugate addition of magnesium cuprates to 2-silyloxycyclopentenecarboxylates leads, after desilylation, to 5-substituted-2-hydroxycyclopentanecarboxylates in high yields and diastereoselectivities. The 2-silyloxy derivatives avoid the formation of the SN 2′ reaction by-products. No loss of sel...
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Published in: | Tetrahedron letters 1996-08, Vol.37 (35), p.6323-6326 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | The conjugate addition of magnesium cuprates to 2-silyloxycyclopentenecarboxylates leads, after desilylation, to 5-substituted-2-hydroxycyclopentanecarboxylates in high yields and diastereoselectivities. The 2-silyloxy derivatives avoid the formation of the SN
2′ reaction by-products. No loss of selectivity is also observed when a catalytic amount of cuprous salt is used.
Conjugate addition of magnesium cuprates to 2-silyloxycyclopentenecarboxylates leads, after desilylation, to 5-substituted-2-hydroxycyclopentanecarboxylates in high yields and diastereoselectivities. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/0040-4039(96)01386-X |