Compendium of Organic Synthetic Methods [Vol 4] by L. Wade

By L. Wade

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JOC 44, 3969 (1979) 88%ee JACS R-CDO 1 )3-pinanyl-9-BBN * 2)HOCH2CH2NH2 R = a1 k y l , a r y l 99, 5211 (1977) 0" RWC-D I H %80% 58-86%ee ,ally1 JACS 101, 2352 (1979) Bu-CHo BuMnI acetone * Bu2CHOH T e t r L e t t , 3383 (1977) 89% 34 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 O " \ '0 A1 / SECTION 34 H 'OEt H Ph-CDO 75% JACS CH3CH2CH0 1 )CH2=CHCH2B(C4H9)2 2) triethanolamine x,3129 (1979) + CH3CH2 \iii OH Bull Acad USSR Chem R = a1 kyl 82%ee , Ph 27, 1663 (1 979) Me Angew Int Ed 3,306 (1979) SECTION 34 35 ALCOHOLS FROM ALDEHYDES B u 3 S n N Ar-CHO * Ar %go% BF3*Et20, CH2C12 A r = Subst.

Me I CH3(CH2)5C02;i -L-Bu Me 0 (coc1)* II CH2 ) 5C-C1 3 DMF CH3 JOC 43, 3'372 (1978) S e c t i o n 24 C a r b o x y l i c Acids f r o m E t hers No a d d i t i o n a l examples 92% S E C T I O N 26 CARBOXYLIC ACIDS FROM HYDRIDES S e c t i o n 25 19 C a r b o x y l i c Acids and A c i d H a l i d e s from A l k y l H a l i d e s 4 0 II (Me3Si)*0 84% c1 c1 JCS Chem Corn, 808 (1977) Also v i a : Esters S e c t i o n 26 - S e c t i o n 115 C a r b o x y l i c Acids from H y d r i w 1 ) LDA ,THF 90% 2)(Me0)2C0 OMe OMe Synthesis, 245 (1977) 20 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 SECTION 27 Q -Carboxylic SECTION 28 Acids from Ketones 8 1 ) NaH, (Et0)2PCH(CN)O-t--Bu 2) ZnC12, Ac20 3) OOH JACS 6 99, 182 ~~70% (1977) Review: "Synthesis of Aldehydes, Ketones, and Carboxylic Acids from Lower Carbonyl Compounds by C-C Coupling Reactions" Synthesis, 633 (1 979) Also via: Esters Section 28 - Section 117.

Section 36 0II Alcohols from Amides t-Bu-C-NMe2 L i Et3BH THF + t-BU-CH20H Synthesis, 635 (1977) 95% ALCOHOLS AND PHENOLS FROM AMINES SECTION 37 1 NaBH4 * -C-lMe NO glyme PhCH20H 37 84% JOC 44, 860 (1979) S e c t i o n 37 A l c o h o l s and Phenols f r o m M i n e s 4 6 JCS P e r k i n I , 1114 (1977) cu20 Cu CH3 2 t ,H20 b CH3 JOC 42, 2053 (1977) 93% COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 38 Section 38 SECTION 38 Alcohols and Phenols from E s t e r s - OH TH F 71% JOC 42, 512 (1977) BH~OP Ph-COOEt 7 PhCH20H 89% JOC 42, 3963 (1977) 0 ‘d- OMEM P-OMEM - COOMEM LiEt3BH T e t r L e t t , 4705 (1979) 90% SECTION 39 ALCOHOLS AND PHENOLS FROM ETHERS AND EPOXIDES 0 \I Li R-O-C-R' * ROH 39 7 1-97% NH3 R ' = Ph o r t-Bu JOC 44, 2810 (1979 fH20Ac ;H20Ac NaBH4 Q O A bMe c 87% * DME OMe Benzyl e s t e r s , benzoates, and cinnamates are unaffected.

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