Hydroxyl-directed reduction of β-hydroxycycloalkanones as a stereoselective route to 1,3-diols: X-ray crystal structure and structural features of (1R*,2R*,6S*)-2-[hydroxy(phenyl)methyl]cyclopentanol
Authors:
- Stephen H. J. ThompsonSTStephen H. J. Thompson
- Mary F. MahonMMMary F. Mahon
- Kieran C. MolloyKMKieran C. Molloy
- Michael S. HadleyMHMichael S. Hadley
- Timothy GallagherTGTimothy Gallagher
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 379-383
Abstract
syn and anti Aldol adducts 4/5 and 6/7 undergo reduction using NaBH(OAc)3 to give 1,3-diols with good to excellent levels of diastereoselectivity. Reduction using NaBH4 is generally less selective but, in the cyclohexyl series, reduction of the syn aldol adduct 6 does afford a complementary stereochemical outcome in relation to the product 1,3-diols obtained. 12vs.13. The structure of the diol 9 has been determined by X-ray crystallographic analysis, thereby providing proof of the stereochemical course of the reduction of the aldol 4. Additionally, the diol 9 is shown to pack in the solid state as columnar stacks of independent hexamers with each pillar comprising a central (OH)6 core, incorporating a network of hydrogen bonds, with a hydrophobic exterior.Keywords
This publication has 25 references indexed in Scilit:
- Chelation-controlled protocol for the diastereoselective reduction of ketonesThe Journal of Organic Chemistry, 1994
- Hydroxy-directed ketone reduction. Application to the synthesis of (+)-8,8a-diepicastanospermineJournal of the Chemical Society, Chemical Communications, 1994
- Enantioselective Aldol and Michael Additions of Achiral Enolates in the Presence of Chiral Lithium Amides and AminesSynthesis, 1993
- An efficient total synthesis of (−)-mintlactone and (+)-isomintlactoneTetrahedron Letters, 1992
- N-substituted pyrrolidin-3-ones as heterocyclic building blocks. Enantioselective synthesis of 8-epi- and 1,8,8a-triepi-castanospermineJournal of the Chemical Society, Chemical Communications, 1992
- Asymmetric aldol reaction: A highly -selective aldol reaction between tricarbonyl(-trimethylsilylbenzaldehyde derivative )-chromium (0) complexes and cyclic silyl enol ethersTetrahedron, 1991
- Directed reduction of .beta.-hydroxy ketones employing tetramethylammonium triacetoxyborohydrideJournal of the American Chemical Society, 1988
- An introduction of chiral centers into acyclic systems based on stereoselective ketone reductionAccounts of Chemical Research, 1984
- Synthesis and configurational and conformational study of the diastereoisomeric 2-(α-hydroxybenzyl)- and 2-(α-methoxybenzyl)-cyclohexanols and some of their derivativesJournal of the Chemical Society, Perkin Transactions 1, 1982
- Chemistry of carbanions. XXIII. Use of metal complexes to control the aldol condensationJournal of the American Chemical Society, 1973