Sp08_215_E1_v3 - 215 Sp 08 E1 p1 I(21 points Complete the...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
215 Sp 08 E1 p1 I ( 21 points ) Complete the following reactions by providing starting material, reactants (number steps as necessary), or products. a) JOC 2008. ASAP Kobayashi O OsO 4 N + O CH 3 O - THF, H 2 O 2) Na 2 SO 3 O HO OH N O O CH 3 N H N OH O CH 3 N H 1) NaBH 4 2) protonation Jones, PCC, PDC, Swern, etc. b) JOC 2008. ASAP Clayden d) JOC , 2008 , ASAP Mandal HO O O O PhCH 2 O H 3 C H NaH O O O O PhCH 2 O H 3 C H I O OH HO HO H H e) Org. Lett. 2008 , 10, 1679 SH HS HCl OH HO HO H H cat. acid O H OH O O H H S S C 15 H 20 O 3 S 2 including 3 6-membered rings S S 3 3 3 3 3 3 3 c) 2008 , 1807 [(CH 3 ) 2 CH] 3 Si OCH 3 H 3 C O H O O 1) CH 3 CH 2 CH 2 CH 2 Li (base) 2) 3) protonation [(CH 3 ) 2 CH] 3 Si OCH 3 H 3 C OH O O 1) + NaI + H 2 intramolecular hemi- acetal w/ 4-hydroxy + H 2 O + H 2 O
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
215 Sp 08 E1 p2 O P Cl H O O H O O H H II ( 30 points ) A. ( JOC 2008 , ASAP, Hartung ) The reagent 2-chloro-bis[menth-1-yloxycarbonyl]-1,3,2- dioxaphospholane was shown to be useful in determining the enatiomeric purity of chiral alcohols via 31 P NMR. The enatiomerically pure phosphorous reagent reacts with chiral alcohols to form diasteromers as shown below. The phosphorous diastereomers have baseline-separated signals. Circle the appropriate stereochemical designation for each stereocenter below. O P O O H O O H O O H H Ph OH Ph 2-chloro-bis[menthy-1-yloxycarbonyl]- 1,3,2-dioxaphospholane R or S R or S R or S R or S R or S In the meso form of 2-chloro-bis[menth-1-yloxycarbonyl]-1,3,2-dioxaphospholane how many of the eight stereocenters would have the opposite configuration from that shown above? (
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Page1 / 5

Sp08_215_E1_v3 - 215 Sp 08 E1 p1 I(21 points Complete the...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online